Molecules having certain pesticidal utilities, and intermediates, compositions, and processes related thereto

ABSTRACT

This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Nematoda, Arthropoda, and/or Mollusca, processes to produce such molecules and intermediates used in such processes, compositions containing such molecules, and processes of using such molecules against such pests. These molecules may be used, for example, as nematicides, acaricides, insecticides, miticides, and/or molluscicides. This document discloses molecules having the following formula (“Formula One”).

CROSS REFERENCE TO RELATED APPLICATIONS

This application claims the benefit of, and priority from, U.S.Provisional Patent Application Ser. No. 62/016,209 filed 24 Jun. 2014,the entire disclosure of which is hereby expressly incorporated byreference.

FIELD OF THE DISCLOSURE

This disclosure relates to the field of molecules having pesticidalutility against pests in Phyla Nematoda, Arthropoda, and Mollusca,processes to produce such molecules and intermediates used in suchprocesses, compositions containing such molecules, and processes ofusing such molecules against such pests. These molecules may be used,for example, as nematicides, acaricides, insecticides, miticides, andmolluscicides.

BACKGROUND OF THE DISCLOSURE

“Many of the most dangerous human diseases are transmitted by insectvectors” (Rivero, A. et al., Insect Control of Vector-Borne Diseases:When is Insect Resistance a Problem? Public Library of SciencePathogens, 6(8) (2010)). Historically, vector-borne diseases, such as,malaria, dengue, yellow fever, plague, and louse-borne typhus, amongothers, were responsible for more human disease and death from the1600's through the early 1900's than all other causes combined (GublerD., Resurgent Vector-Borne Diseases as a Global Health Problem, EmergingInfectious Diseases, Vol. 4, No. 3, July-September (1998)). Currently,vector-borne diseases are responsible for about 17% of the globalparasitic and infectious diseases. It has been estimated that about 250million people around the world have malaria and about 800,000 deathsoccur each year—85% of those deaths are children under the age of five.A further 250,000 to 500,000 cases of dengue hemorrhagic fever occureach year (Matthews, G., Integrated Vector Management: controllingvectors of malaria and other insect vector borne diseases (2011)).Vector control plays a critical role in the prevention and control ofinfectious diseases. However, insecticide resistance, includingresistance to multiple insecticides, has arisen in all insect speciesthat are major vectors of human diseases (Rivero, A. et al.).

Each year insects, plant pathogens, and weeds destroy more than 40% ofall potential food production. This loss occurs despite the applicationof pesticides and the use of a wide array of non-chemical controls, suchas crop rotations and biological controls. If just some of this foodcould be saved, it could be used to feed the more than three billionpeople in the world who are malnourished (Pimental, D., Pest Control inWorld Agriculture, Agricultural Sciences—Vol. II (2009)).

Plant parasitic nematodes are among the most widespread pests, and arefrequently one of the most insidious and costly. It has been estimatedthat losses attributable to nematodes are from about 9% in developedcountries to about 15% in undeveloped countries. However, in the UnitedStates of America, a survey of 35 States on various crops indicatednematode-derived losses of up to 25% (Nicol, J. et al., Current NematodeThreats to World Agriculture, Genomic and Molecular Genetics ofPlant—Nematode Interactions (Eds. Jones, J. et al.), Chapter 2, (2011)).

It is noted that gastropods (slugs and snails) are pests of lesseconomic importance than insects or nematodes, but in certain areas,gastropods may reduce yields substantially, severely affecting thequality of harvested products, as well as transmitting human, animal,and plant diseases. While only a few dozen species of gastropods areserious regional pests, a handful of species are important pests on aworld-wide scale. In particular, gastropods affect a wide variety ofagricultural and horticultural crops, such as arable, pastoral, andfiber crops; vegetables; bush and tree fruits; herbs; and ornamentals(Speiser, B., Molluscicides, Encyclopedia of Pest Management (2002)).

Termites cause damage to all kinds of private and public structures, aswell as to agricultural and forestry resources. In 2003, it wasestimated that termites cause over US$20 billion in damage world-wideeach year (Su, N.Y., Overview of the global distribution and control ofthe Formosan subterranean termite, Sociobiology 2003, 41, 177-192).

Therefore, for many reasons, including the above reasons, a need existsfor new pesticides.

DEFINITIONS

The examples given in the definitions are generally non-exhaustive andmust not be construed as limiting the molecules disclosed in thisdocument. It is understood that a substituent should comply withchemical bonding rules and steric compatibility constraints in relationto the particular molecule to which it is attached.

“Alkenyl” means an acyclic, unsaturated (at least one carbon-carbondouble bond), branched or unbranched, substituent consisting of carbonand hydrogen, for example, vinyl, allyl, butenyl, pentenyl, and hexenyl.

“Alkoxy” means an alkyl further consisting of a carbon-oxygen singlebond, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy,isobutoxy, and tert-butoxy.

“Alkyl” means an acyclic, saturated, branched or unbranched, substituentconsisting of carbon and hydrogen, for example, methyl, ethyl, propyl,isopropyl, butyl, and tert-butyl.

“Cycloalkyl” means a monocyclic or polycyclic, saturated substituentconsisting of carbon and hydrogen, for example, cyclopropyl, cyclobutyl,cyclopentyl, norbornyl, bicyclo[2.2.2]octyl, and decahydronaphthyl.

“Halo” means fluoro, chloro, bromo, and iodo.

“Haloalkoxy” means an alkoxy further consisting of, from one to themaximum possible number of identical or different, halos, for example,fluoromethoxy, trifluoromethoxy, 2,2-difluoropropoxy, chloromethoxy,trichloromethoxy, 1,1,2,2-tetrafluoroethoxy, and pentafluoroethoxy.

“Haloalkyl” means an alkyl further consisting of, from one to themaximum possible number of, identical or different, halos, for example,fluoromethyl, trifluoromethyl, 2,2-difluoropropyl, chloromethyl,trichloromethyl, and 1,1,2,2-tetrafluoroethyl.

DETAILED DESCRIPTION OF THE DISCLOSURE

This document discloses molecules having the following formula (“FormulaOne”)

wherein:

(A) R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁹, and R¹⁰ are, each independently, H,F, Cl, Br, I, CN, NO₂, OH, (C₁-C₄)alkyl, (C₂-C₄)alkenyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, or(C₃-C₆)cycloalkyl, wherein each alkyl, alkenyl, haloalkyl, alkoxy,haloalkoxy, and cycloalkyl, is optionally substituted with one or moresubstituents, wherein each substituent is independently H, F, Cl, Br, I,CN, NO₂, OH, (C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₁-C₄)haloalkyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, or (C₃-C₆)cycloalkyl;

(B) R⁸ is H;

(C) L is a linker that is C₁-C₄ alkyl, C₂-C₄ alkenyl, or C₁-C₄haloalkyl, wherein each alkyl, alkenyl, and haloalkyl, is optionallysubstituted with one or more substituents, wherein each substituent isindependently F, Cl, CN, OH, or oxo;

(D) R¹¹, R¹², R¹³, R¹⁴, and R¹⁵ are, each independently, H, F, Cl, Br,I, CN, NO₂, OH, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, or(C₁-C₄)haloalkoxy, wherein each alkyl, alkoxy, and haloalkyl, isoptionally substituted with one or more substituents, wherein eachsubstituent is independently F, Cl, CN, OH, or oxo; and

(E) Q is O or S.

In another embodiment R¹, R², R³, R⁴, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹⁴, and R¹⁵are H. This embodiment may be used in combination with the otherembodiments of R⁵, R¹¹, R¹², R¹³, L, and Q.

In another embodiment R⁵ is OCF₃ or CF₃. This embodiment may be used incombination with the other embodiments of R¹, R², R³, R⁴, R⁶, R⁷, R⁸,R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, L, and Q.

In another embodiment L is —CH₂— or —CH₂CH₂—. This embodiment may beused in combination with the other embodiments of R¹, R², R³, R⁴, R⁵,R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, and Q.

In another embodiment R¹¹, R¹², and R¹³ are, each independently, H, F,Cl, Br, or I. This embodiment may be used in combination with the otherembodiments of R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹⁴, R¹⁵, L, andQ.

In another embodiment R¹² is CH₃. This embodiment may be used incombination with the other embodiments of R¹, R², R³, R⁴, R⁵, R⁶, R⁷,R⁸, R⁹, R¹⁰, R¹¹, R¹³, R¹⁴, R¹⁵, L, and Q.

In another embodiment R¹³ is CH₃, OCH₃, CF₃, or OCF₃. This embodimentmay be used in combination with the other embodiments of R¹, R², R³, R⁴,R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹⁴, R¹⁵, L, and Q.

In another embodiment:

(A) R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁹, and R¹⁰ are, each independently, H,C₁-C₄ haloalkyl, or C₁-C₄ haloalkoxy;

(B) R⁸ is H;

(C) L is a linker that is C₁-C₄ alkyl;

(D) R¹¹, R¹², R¹³, R¹⁴, and R¹⁵ are, each independently, H, F, Cl, Br,C₁-C₄ alkyl, C₁-C₄ haloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; and

(E) Q is selected from O or S.

In another embodiment:

(A) R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁹, and R¹⁰ are, each independently, H,C₁-C₄ haloalkyl, or C₁-C₄ haloalkoxy;

(B) R⁸ is H;

(C) L is a linker that is C₁-C₄ alkyl;

(D) R¹¹, R¹², R¹³, R¹⁴, and R¹⁵ are, each independently, H, Cl, Br,C₁-C₄ haloalkyl, or C1-C4 haloalkoxy; and

(E) Q is O.

Preparation of 2-amino-oxazolines, 2-amino-oxazinanes, and2-amino-thiazolines

2-Amino-oxazolines 1-2, wherein Q is O, L is —CH₂—, and R¹, R², R³, R⁴,R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, and R¹⁵ are as previouslydisclosed; 2-amino-oxazinanes 1-2, wherein Q is O, L is —CH₂CH₂—, andR¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, and R¹⁵ areas previously disclosed; and 2-amino-thiazolines 1-3, wherein Q is S, Lis —CH₂—, and R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³,R¹⁴, and R¹⁵ are as previously disclosed, may be prepared from thecorresponding triaryl thioureas 1-1, wherein Q is S, L is —CH₂— or—CH₂CH₂—, and R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³,R¹⁴, and R¹⁵ are as previously disclosed. Treatment of thioureas 1-1with para-toluenesulfonyl chloride in a mixed solvent system of anaprotic solvent, such as dichloromethane, diethyl ether, ortetrahydrofuran and water, in the presence of an inorganic base, such assodium hydroxide, at temperatures from about 10° C. to about 30° C. mayprovide 2-amino-oxazolines 1-2, wherein L is —CH₂—, or2-amino-oxazinanes 1-2, wherein L is —CH₂CH₂— (Scheme 1, step a). In apreferred embodiment, the inorganic base may be added as an aqueoussolution. In a similar fashion, the 2-amino-thiazolines 1-3 may beprepared by treating thioureas 1-1 with carbodiimidazole in an aproticsolvent, such as diethyl ether or tetrahydrofuran, at temperatures fromabout 10° C. to about 30° C. (Scheme 1, step b).

Preparation of Thioureas

Usually, thioureas 1-1 are generated from a precursor, such asisothiocyanates 2-1, wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, and R¹⁰are as previously disclosed, which may be converted into thioureas 1-1by treatment with amino alcohols 2-2, wherein L is —CH₂— or —CH₂CH₂—,and R¹¹, R¹², R¹³, R¹⁴, and R¹⁵ are as previously disclosed, in a mixedsolvent system of an aprotic solvent such as tetrahydrofuran, in thepresence of an organic base such as triethylamine, at temperatures fromabout −10° C. to about 65° C. (Scheme 2, step a).

Preparation of Isothiocyanates

Isothiocyanates 2-1 used to prepare thioureas 1-1 may be prepared fromthe corresponding triaryl amines 3-1, wherein R¹, R², R³, R⁴, R⁵, R⁶,R⁷, R⁸, R⁹, and R¹⁰ are as previously disclosed. Treatment of triarylamines 3-1 with thiophosgene or thiocarbodiimidazole, preferablythiophosgene, in a mixed solvent system of an aprotic solvent such asdichloromethane and water, in the presence of an inorganic base such assodium bicarbonate, at temperatures from about 10° C. to about 30° C.may provide isothiocyanates 2-1 (Scheme 3, step a).

Alternatively, triaryl amines 3-1 may be treated with carbon disulfide,with or without a solvent, in the presence of an organic base such astriethylamine at temperatures from about 40° C. to about 60° C. to formcarbamodithioate 3-2, wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, andR¹⁰ are as previously disclosed (Scheme 3, step b). Subsequent treatmentof carbamodithioates 3-2 with a carbodiimide, such asdicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide,or preferably diisopropylcarbodiimide in a polar aprotic solvent such asacetonitrile, at temperatures from about 10° C. to about 30° C. mayprovide isothiocyanates 2-1 (Scheme 3, step c).

Preparation of Triaryl Amine-Intermediates

Molecules of formula one may be prepared by making triaryl amines 3-1.These triaryl amines may be prepared by methods previously described inthe chemical literature, including Crouse, et al., PCT Int. Appl. Publ.WO2009/102736 A1 (the entire disclosure of which is hereby incorporatedby reference). 3-(4-Nitrophenyl)-1,2,4-triazole 4-2, wherein R¹, R², R⁸,R⁹, and R¹⁰ are as previously disclosed may be prepared in two stepsfrom 4-nitrobenzamide 4-1, wherein R¹, R², R⁹, and R¹⁰ are as previouslydisclosed, under conditions described previously (Crouse, et. al.,WO2009102736) (Scheme 4, step a). Triazoles 4-2 may then be coupled toan aryl halide 4-3, wherein R³, R⁴, R⁵, R⁶, and R⁷ areas previouslydisclosed, such as 4-trifluoromethylphenyl bromobenzene, in the presenceof cesium carbonate or potassium phosphate, in a polar aprotic solventsuch as dimethylformamide.

This reaction may be catalyzed by a copper salt such as copper(I) iodideand a chelator such as 8-hydroxyquinoline, both present in about 0.05 toabout 0.25 equivalents, at a temperature ranging between about 80° C.and about 140° C., to form the (4-nitrophenyl) triazoles 4-4, whereinR¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, and R¹⁰ are as previously disclosed(Scheme 4, step b). Reduction of the (4-nitrophenyl)triazoles 4-4 may beachieved by treatment with a metal, such as iron, in an acidic medium,such as acetic acid, at temperatures from about 50° C. to about 100° C.to provide triaryl amines 3-1 (Scheme 3, step c).

Preparation of Amine Alcohol-Intermediates

Molecules of formula one may be prepared by making amino alcohols 2-2.Treatment of amino acids 5-1, wherein R¹¹, R¹², R¹³, R¹⁴, and R¹⁵ are aspreviously disclosed, with lithium aluminum hydride in a polar aproticsolvent, such as tetrahydrofuran at temperatures from about 50° C. toabout 65° C. may provide amino alcohols 2-2 (Scheme 5, step a).

EXAMPLES

These examples are for illustration purposes and are not to be construedas limiting the disclosure to only the embodiments disclosed in theseexamples.

Starting materials, reagents, and solvents that were obtained fromcommercial sources were used without further purification. Anhydroussolvents were purchased as Sure/Seal™ from Aldrich and were used asreceived. Melting points were obtained on a Thomas Hoover Unimeltcapillary melting point apparatus or an OptiMelt Automated Melting PointSystem from Stanford Research Systems and are uncorrected. Examplesusing “room temperature” were conducted in climate controlledlaboratories with temperatures ranging from about 20° C. to about 24° C.Molecules are given their known names, named according to namingprograms within ISIS Draw, ChemDraw or ACD Name Pro. If such programsare unable to name a molecule, the molecule is named using conventionalnaming rules. ¹H NMR spectral data are in ppm (δ) and were recorded at300, 400 or 600 MHz, and ¹³C NMR spectral data are in ppm (δ) and wererecorded at 75, 100 or 150 MHz, unless otherwise stated.

Example 1 Preparation of3-(4-nitrophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazole (C1)

A mixture of 3-(4-nitrophenyl)-1H-1,2,4-triazole (20.0 g, 105 mmol),1-bromo-4-(trifluoromethyl)benzene (28.0 g, 124 mmol), cesium carbonate(68.4 g, 210 mmol), copper(I) iodide (2.59 g, 13.6 mmol), and8-hydroxyquinoline (1.80 g, 12.4 mmol) in N,N′-dimethylformamide/water(9:1, 142 mL) under nitrogen was heated to 140° C. for 18 hours. Thereaction was cooled to room temperature (about 22° C.) and quenched withammonium hydroxide (10 mL). The reaction mixture was extracted withethyl acetate. The organic layer was separated and washed with water(3×100 mL) and brine (300 mL). The organic layer was separated and driedover sodium sulfate, filtered, and concentrated. Purification by flashcolumn chromatography (silica gel) using 0-65% ethyl acetate/petroleumether as eluent provided the title compound as a white solid (22.0 g,63%): ¹H NMR (300 MHz, CDCl₃) δ 8.72 (s, 1H), 8.42-8.34 (m, 4H), 7.94(d, J=8.7 Hz, 2H), 7.84 (d, J=8.5 Hz, 2H); ESIMS m/z 335 ([M+H]⁺).

Example 2 Preparation of4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)aniline (C2)

To 3-(4-nitrophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazole(22.0 g, 65.8 mmol) in acetic acid (132 mL) and water (110 mL) was addediron powder. The reaction was heated to 90° C. for 18 hours. Thereaction was cooled to room temperature and filtered through Celite®followed by an ethyl acetate wash. The organic layer was separated andconcentrated. Purification by flash column chromatography using 0-50%ethyl acetate/petroleum ether as eluent provided the title compound as alight yellow solid (15.6 g, 74%): ¹H NMR (300 MHz, CDCl₃) δ 8.00 (d,J=1.0 Hz, 1H), 7.68-6.92 (m, 6H), 6.29-5.93 (m, 2H), 3.27 (bs, 2H);ESIMS m/z 305 ([M+H]⁺).

Example 3 Preparation of3-(4-isothiocyanatophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazole(C3)

Prepared according to the procedure reported in (WO 2011017513) for3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazolefrom 4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)aniline andisolated as a white solid (10.6 g, 94%): ¹H NMR (300 MHz, CDCl₃) δ 8.07(s, 1H), 7.73-7.41 (m, 2H), 7.41-7.05 (m, 4H), 6.92-6.63 (m, 2H); ESIMSm/z 347 ([M+H]⁺).

Example 4 Preparation of 2-amino-2-(4-chloro-3-methylphenyl)ethanol (C4)

To 2-amino-2-(4-chloro-3-methylphenyl)acetic acid (1.7 g, 8.5 mmol) intetrahydrofuran (0.4 M) at 0° C. was added lithium aluminum hydride (2M, 8.5 mL, 17 mmol) dropwise. The reaction was refluxed for 18 hours.The reaction was cooled and quenched with ice water. The reaction wasextracted with ethyl acetate, washed with water, and brine. The combinedorganic layers were dried over sodium sulfate, filtered, andconcentrated to provide the title compound as a yellow solid (1.6 g,quantitative): ¹H NMR (300 MHz, DMSO-d₆) δ 7.44-7.23 (m, 2H), 7.18 (dd,J=8.2, 2.2 Hz, 1H), 4.77 (bs, 2H), 3.81 (dd, J=7.8, 4.8 Hz, 1H),3.53-3.14 (m, 3H), 2.30 (s, 3H); ESIMS m/z 186 ([M+H]⁺).

Example 5 General Procedure for the Preparation of Thioureas

To a stirred solution of amino alcohol (1.0 eq) in dry tetrahydrofuran(20 vol) was added the appropriate isothiocyanate (1.0 eq) andtriethylamine (1.5 eq). The reaction mixture was heated at 50° C. for 12hours. The reaction mixture was concentrated under reduced pressure.Purification by flash column chromatography provided the titlecompounds.

The following compounds were prepared according to the proceduresdisclosed in Example 5:

(R)-1-(2-Hydroxy-1-phenylethyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea(C5)

The title compound was prepared with (R)-2-amino-2-phenylethanol and3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazole(Lambert, W.; et al., WO 2011017513) and isolated as an off-white solid(0.285 g, 69%): mp 98-101° C.; ¹H NMR (400 MHz, DMSO-d₆) δ 9.99 (s, 1H),9.37 (s, 1H), 8.40 (d, J=7.9 Hz, 1H), 8.07-8.01 (m, 4H), 7.73 (d, J=7.7Hz, 2H), 7.61 (d, J=8.5 Hz, 2H), 7.38-7.24 (m, 5H), 5.42 (s, 1H), 5.12(s, 1H), 3.73 (s, 2H); ESIMS m/z 500 ([M+H]⁺).

1-(1-(4-Chlorophenyl)-2-hydroxyethyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea(C6)

The title compound was prepared with 2-amino-2-(4-chlorophenyl)ethanol(Chen, L.; et al., US 20060004045) and3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazoleand isolated as an off-white solid (0.300 g, 68%): mp 94-97° C.; ¹H NMR(300 MHz, CD₃OD) δ 9.12 (s, 1H), 8.11 (d, J=6.8 Hz, 2H), 8.01 (d, J=6.9Hz, 2H), 7.61 (d, J=8.6 Hz, 2H), 7.49 (d, J=8.3 Hz, 3H), 7.32-7.38 (m,3H), 5.59 (s, 1H), 3.84-3.87 (m, 2H) (NH, OH not observed); ESIMS m/z534 ([M+H]⁺).

1-(2-Hydroxy-1-(p-tolyl)ethyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea(C7)

The title compound was prepared with 2-amino-2-(p-tolyl)ethanol and3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazoleand isolated as an off-white solid (0.300 g, 71%): mp 145-156° C.; ¹HNMR (400 MHz, CD₃OD) δ 9.13 (s, 1H), 8.12 (d, J=6.8 Hz, 2H), 8.05 (d,J=2.2 Hz, 2H), 7.65 (d, J=7.4 Hz, 2H), 7.51 (d, J=8.2 Hz, 2H), 7.24-7.23(m, 2H), 7.18-7.16 (m, 2H), 5.60 (s, 1H), 3.90-3.84 (m, 2H), 2.34 (s,3H) (NH, OH not observed); ESIMS m/z 514 ([M+H]⁺).

1-(2-Hydroxy-1-(4-(trifluoromethyl)phenyl)ethyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea(C8)

The title compound was prepared with2-amino-2-(4-(trifluoromethyl)phenyl)ethanol and3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazoleand isolated as an off-white solid (0.250 g, 53%): ESIMS m/z 568([M+H]⁺).

(S)-1-(2-Hydroxy-1-phenylethyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea(C9)

The title compound was prepared with (S)-2-amino-2-phenylethanol and3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazoleand isolated as an off-white solid (0.300 g, 73%): mp 125-128° C.; ¹HNMR (400 MHz, CD₃OD) δ 9.14 (s, 1H), 8.13 (d, J=8.3 Hz, 2H), 8.04 (d,J=8.8 Hz, 2H), 7.64 (d, J=8.3 Hz, 2H), 7.51 (d, J=8.7 Hz, 2H), 7.43-7.35(m, 4H), 7.30-7.27 (m, 1H), 5.64 (s, 1H), 3.94-3.86 (m, 2H) (NH, OH notobserved); ESIMS m/z 500 ([M+H]⁺).

(R)-1-(3-Hydroxy-1-phenylpropyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea(C10)

The title compound was prepared with (R)-3-amino-3-phenylpropan-1-ol and3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazoleand isolated as an off-white solid (0.270 g, 64%): mp 162-165° C.; ¹HNMR (400 MHz, DMSO-d₆) δ 9.74 (s, 1H), 9.37 (d, J=1.8 Hz, 1H), 8.42 (d,J=7.6 Hz, 1H), 8.07-8.01 (m, 4H), 7.63-7.61 (m, 4H), 7.35-7.34 (m, 4H),7.25-7.26 (m, 1H), 5.58 (s, 1H), 4.65 (s, 1H), 3.39-3.40 (m, 2H),1.90-2.03 (m, 2H); ESIMS m/z 514 ([M+H]⁺).

Example 6 Preparation of1-(2-hydroxy-1-(4-methoxyphenyl)ethyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea(C11)

To3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazole(1.09 g, 2.70 mmol) in tetrahydrofuran (7 mL) was added2-amino-2-(4-methoxyphenyl)ethanol (0.506 g, 3.30 mmol) (Reggelin, M. etal., Synlett, 2012, 23, 1095-1098). The reaction was stirred overnightat room temperature. The reaction mixture was concentrated and theresidue was recrystallized with petroleum ether providing the titlecompound as a white solid (1.42 g, 81%): ¹H NMR (300 MHz, CDCl₃) δ 7.96(s, 1H), 7.72-7.57 (m, 2H), 7.27 (s, 1H), 7.23-7.14 (m, 2H), 6.87-6.72(m, 4H), 6.64-6.56 (m, 2H), 6.38-6.22 (m, 3H), 5.05 (s, 1H), 3.47-3.28(m, 2H), 3.20 (s, 3H); ESIMS m/z 530 ([M+H]⁺).

The following compounds were prepared according to the proceduresdisclosed in Example 6:

1-(1-(4-Fluorophenyl)-2-hydroxyethyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea(C12)

The title compound was prepared with 2-amino-2-(4-fluorophenyl)ethanoland3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazoleand isolated as an off-white solid (1.42 g, 81%): ¹H NMR (300 MHz,CDCl₃) δ 7.96 (s, 1H), 7.72-7.57 (m, 2H), 7.27 (s, 1H), 7.23-7.14 (m,2H), 6.87-6.72 (m, 4H), 6.64-6.56 (m, 2H), 6.38-6.22 (m, 3H), 5.05 (s,1H), 3.47-3.28 (m, 2H), 3.20 (s, 3H); ESIMS m/z 530 ([M+H]⁺).

1-(1-(4-Bromophenyl)-2-hydroxyethyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea(C13)

The title compound was prepared with 2-amino-2-(4-bromophenyl)ethanol(Chen, L.; et al., US 20060004045) and3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazoleand isolated as a white solid (1.58 g, 98%): ¹H NMR (400 MHz, CDCl₃) δ8.60 (s, 1H), 8.41-8.05 (m, 3H), 8.03-7.68 (m, 2H), 7.68-6.95 (m, 10H),5.88-5.44 (m, 1H), 4.25-3.80 (m, 2H); ESIMS m/z 578 ([M+H]⁺).

1-(2-Hydroxy-1-(4-(trifluoromethoxy)phenyl)ethyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea(C14)

The title compound was prepared with2-amino-2-(4-(trifluoromethoxy)phenyl)ethanol and3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazoleand isolated as an white solid (1.42 g, 87%) ¹H NMR (400 MHz, CDCl₃) δ8.60 (s, 1H), 8.35-8.22 (m, 2H), 7.94 (s, 1H), 7.88-7.71 (m, 2H),7.51-7.11 (m, 9H), 7.05 (d, J=7.9 Hz, 1H), 5.75 (s, 1H), 4.06 (dd,J=11.2, 3.9 Hz, 1H), 3.94 (dd, J=11.2, 4.7 Hz, 1H); ESIMS m/z 584([M+H]⁺).

1-(1-(3-Chlorophenyl)-2-hydroxyethyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea(C15)

The title compound was prepared with 2-amino-2-(3-chlorophenyl)ethanol(Galley, G.; et al., WO 2008092785) and3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazoleand isolated as an white solid (1.44 g, 99%): ¹H NMR (300 MHz, CDCl₃) δ7.96 (s, 1H), 7.66-7.53 (m, 3H), 7.25-7.08 (m, 2H), 6.77 (dd, J=8.6, 6.3Hz, 4H), 6.70-6.61 (m, 4H), 6.58 (dd, J=6.4, 2.2 Hz, 1H), 6.49 (d, J=7.8Hz, 1H), 5.18-4.95 (m, 1H), 3.43 (dd, J=11.3, 3.9 Hz, 1H), 3.31 (dd,J=11.3, 4.6 Hz, 1H); ESIMS m/z 534 ([M+H]⁺).

1-(1-(2-Chlorophenyl)-2-hydroxyethyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea(C16)

The title compound was prepared with 2-amino-2-(2-chlorophenyl)ethanol(Brueggemeier, U.; et al., WO 2010105770) and3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazoleand isolated as a white solid (1.44 g, quantitative): ¹H NMR (300 MHz,CDCl₃) δ 7.97 (d, J=1.1 Hz, 1H), 7.64 (d, J=8.2 Hz, 1H), 7.47-7.41 (m,1H), 7.23-7.13 (m, 2H), 6.87-6.55 (m, 11H), 5.39 (d, J=8.3 Hz, 1H),3.48-3.30 (m, 2H).

1-(2-Hydroxy-1-(4-methoxyphenyl)ethyl)-3-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea(C17)

The title compound was prepared with 2-amino-2-(4-methoxyphenyl)ethanoland3-(4-isothiocyanatophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazoleand isolated as a white solid (1.42 g, quantitative): ¹H NMR (300 MHz,CDCl₃) δ 8.06 (s, 1H), 7.66 (d, J=8.3 Hz, 2H), 7.31 (d, J=8.5 Hz, 2H),7.21 (d, J=8.1 Hz, 3H), 6.76 (d, J=8.3 Hz, 2H), 6.66 (s, 3H), 6.30 (d,J=8.2 Hz, 3H), 5.19-5.01 (m, 1H), 3.50-3.23 (m, 2H), 3.20 (s, 3H); ESIMSm/z 514 ([M+H]⁺).

1-(2-Hydroxy-1-(p-tolyl)ethyl)-3-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea(C18)

The title compound was prepared with 2-amino-2-(p-tolyl)ethanol and3-(4-isothiocyanatophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazoleand isolated as a white solid (1.39 g, 99%): ¹H NMR (300 MHz, CDCl₃) δ8.06 (s, 1H), 7.66 (d, J=8.4 Hz, 2H), 7.31 (d, J=8.7 Hz, 2H), 7.21 (d,J=8.6 Hz, 2H), 6.76 (t, J=8.5 Hz, 2H), 6.63-6.49 (m, 7H), 5.12-5.00 (m,1H), 3.56-3.08 (m, 2H), 1.73 (s, 3H); ESIMS m/z 498 ([M+H]⁺).

1-(2-Hydroxy-1-phenylethyl)-3-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea(C19)

The title compound was prepared with 2-amino-2-phenylethanol and3-(4-isothiocyanatophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazoleand isolated as a white solid (1.36 g, quantitative): ¹H NMR (300 MHz,CDCl₃) δ 8.05 (s, 1H), 7.65 (d, J=8.4 Hz, 2H), 7.38 (d, J=4.6 Hz, 1H),7.30 (d, J=8.5 Hz, 2H), 7.20 (d, J=8.6 Hz, 2H), 6.88-6.61 (m, 8H), 6.43(d, J=7.9 Hz, 1H), 5.22-4.90 (m, 1H), 3.46-3.28 (m, 2H); ESIMS m/z 484([M+H]⁺).

1-(1-(4-Fluorophenyl)-2-hydroxyethyl)-3-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea(C20)

The title compound was prepared with 2-amino-2-(4-fluorophenyl)ethanoland3-(4-isothiocyanatophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazoleand isolated as a white solid (1.4 g, 99%): ¹H NMR (300 MHz, CDCl₃) δ8.07 (s, 1H), 7.67 (d, J=8.1 Hz, 2H), 7.31 (d, J=8.4 Hz, 2H), 7.21 (d,J=8.6 Hz, 2H), 6.82-6.67 (m, 4H), 6.44 (q, J=7.7, 7.1 Hz, 4H), 6.33 (d,J=8.3 Hz, 1H), 5.09 (s, 1H), 3.44 (dd, J=10.9, 4.2 Hz, 1H), 3.32 (dd,J=11.2, 4.7 Hz, 1H); ESIMS m/z 502 ([M+H]⁺).

1-(1-(4-Chlorophenyl)-2-hydroxyethyl)-3-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea(C21)

The title compound was prepared with 2-amino-2-(4-chlorophenyl)ethanoland3-(4-isothiocyanatophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazoleand isolated as a white solid (1.4 g, 97%): ¹H NMR (300 MHz, CDCl₃) δ8.06 (s, 1H), 7.67 (d, J=8.5 Hz, 2H), 7.31 (d, J=8.7 Hz, 2H), 7.21 (d,J=7.7 Hz, 2H), 6.81-6.51 (m, 8H), 6.41 (s, 1H), 5.70-5.44 (m, 1H),3.20-2.82 (m, 2H); ESIMS m/z 518 ([M+H]⁺).

1-(1-(4-Bromophenyl)-2-hydroxyethyl)-3-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea(C22)

The title compound was prepared with 2-amino-2-(4-bromophenyl)ethanoland3-(4-isothiocyanatophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazoleand isolated as a white solid (1.56 g, 99%): ¹H NMR (400 MHz, CDCl₃) δ8.72 (s, 1H), 8.32-8.22 (m, 2H), 7.92 (d, J=8.0 Hz, 2H), 7.82 (d, J=8.4Hz, 2H), 7.45-7.28 (m, 8H), 7.20 (d, J=8.0 Hz, 1H), 5.69 (s, 1H),4.11-3.86 (m, 2H); ESIMS m/z 562 ([M+H]⁺).

1-(2-Hydroxy-1-(4-(trifluoromethyl)phenyl)ethyl)-3-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea(C23)

The title compound was prepared with2-amino-2-(4-(trifluoromethyl)phenyl)ethanol and3-(4-isothiocyanatophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazoleand isolated as a white solid (1.54 g, quantitative): ¹H NMR (300 MHz,CDCl₃) δ 8.09 (s, 1H), 7.66 (d, J=8.7 Hz, 2H), 7.43 (d, J=6.3 Hz, 1H),7.30 (d, J=8.4 Hz, 2H), 7.20 (d, J=8.6 Hz, 2H), 7.02 (d, J=8.2 Hz, 2H),6.88-6.69 (m, 4H), 6.61-6.50 (m, 2H), 5.27-5.07 (m, 1H), 3.48-3.40 (m,1H), 3.40-3.24 (m, 1H); ESIMS m/z 552 ([M+H]⁺).

1-(2-Hydroxy-1-(4-(trifluoromethoxy)phenyl)ethyl)-3-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea(C24)

The title compound was prepared with2-amino-2-(4-(trifluoromethoxy)phenyl)ethanol and3-(4-isothiocyanatophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazoleand isolated as a white solid (1.58 g, 99%): ¹H NMR (300 MHz, CDCl₃) δ8.07 (s, 1H), 7.67 (d, J=8.5 Hz, 2H), 7.37-7.26 (m, 3H), 7.21 (d, J=8.6Hz, 2H), 6.76 (dd, J=11.6, 8.6 Hz, 4H), 6.64-6.56 (m, 3H), 6.43 (d,J=7.9 Hz, 1H), 5.13 (s, 1H), 3.45 (dd, J=11.2, 4.0 Hz, 1H), 3.33 (dd,J=11.2, 4.5 Hz, 1H); ESIMS m/z 568 ([M+H]⁺).

1-(1-(3-Chlorophenyl)-2-hydroxyethyl)-3-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea(C25)

The title compound was prepared with 2-amino-2-(3-chlorophenyl)ethanoland3-(4-isothiocyanatophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazoleand isolated as a white solid (1.48 g, quantitative): ¹H NMR (300 MHz,CDCl₃) δ 8.07 (s, 1H), 7.69 (d, J=8.4 Hz, 2H), 7.31 (d, J=8.7 Hz, 3H),7.21 (d, J=8.5 Hz, 2H), 6.83-6.72 (m, 3H), 6.67 (d, J=7.3 Hz, 4H), 6.39(d, J=7.9 Hz, 1H), 5.09 (s, 1H), 3.14 (dd, J=10.7, 4.4 Hz, 1H), 2.93(dd, J=10.7, 8.0 Hz, 1H); ESIMS m/z 518 ([M+H]⁺).

1-(1-(2-Chlorophenyl)-2-hydroxyethyl)-3-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea(C26)

The title compound was prepared with 2-amino-2-(2-chlorophenyl)ethanoland3-(4-isothiocyanatophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazoleand isolated as a white solid (1.48 g, quantitative): ¹H NMR (300 MHz,CDCl₃) δ 8.07 (s, 1H), 7.77-7.55 (m, 2H), 7.41-7.23 (m, 3H), 7.21 (d,J=8.5 Hz, 2H), 6.81 (dd, J=8.7, 2.6 Hz, 2H), 6.65 (d, J=6.8 Hz, 6H),5.40 (s, 1H), 3.39 (qd, J=11.6, 4.9 Hz, 2H); ESIMS m/z 518 ([M+H]⁺).

Example 7 General Procedure for the Preparation of 2-Amino Oxazolinesand 2-Amino Oxazinanes

To a stirred solution of appropriate thiourea (1.0 eq) intetrahydrofuran (10 vol) was added a sodium hydroxide solution (2M, 2.5eq) and p-toluenesulfonyl chloride (1.1 eq) in tetrahydrofuran (5 vol).The reaction mixture was stirred at room temperature for 12 h. Thereaction mixture was concentrated under reduced pressure, diluted withwater, and extracted with ethyl acetate. The combined organic layerswere washed with water, saturated brine solution, dried over anhydroussodium sulfate and concentrated under reduced pressure. Purification byflash column chromatography or recrystallization provided the titlecompounds.

The following compounds were prepared according to the proceduresdisclosed in Example 7:

(R)-4-Phenyl-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrooxazol-2-amine(F1)

Isolated as an off-white solid (0.150 g, 65%).

(S)-4-Phenyl-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrooxazol-2-amine(F2)

Isolated as an off-white solid (0.150 g, 65%).

4-(4-Chlorophenyl)-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrooxazol-2-amine(F3)

Isolated as an off-white solid (0.025 g, 11%).

4-(p-Tolyl)-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrooxazol-2-amine(F4)

Isolated as an off-white solid (0.035 g, 15%).

N-(4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4-(4-(trifluoromethyl)phenyl)-4,5-dihydrooxazol-2-amine(F5)

Isolated as an off-white solid (0.100 g, 43%).

4-(4-Methoxyphenyl)-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrooxazol-2-amine(F6)

Isolated as a white solid (0.59 g, 92%).

4-(4-Fluorophenyl)-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrooxazol-2-amine(F8)

Isolated as a white solid (0.27 g, 59%).

4-(4-Bromophenyl)-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrooxazol-2-amine(F9)

Isolated as a white solid (0.156 g, %).

4-(3-Chlorophenyl)-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrooxazol-2-amine(F10)

Isolated as a white solid (0.5 g, 76%).

4-(2-Chlorophenyl)-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrooxazol-2-amine(F11)

Isolated as a white solid (0.5 g, 78%).

4-(4-Methoxyphenyl)-N-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrooxazol-2-amine(F12)

Isolated as a white solid (0.33 g, 50%).

4-(p-Tolyl)-N-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrooxazol-2-amine(F13)

Isolated as a white solid (0.58 g, 92%).

4-Phenyl-N-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrooxazol-2-amine(F14)

Isolated as a white solid (0.57 g, 92%).

4-(4-Fluorophenyl)-N-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrooxazol-2-amine(F15)

Isolated as a white solid (0.47 g, 73%).

4-(4-Chlorophenyl)-N-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrooxazol-2-amine(F16)

Isolated as a white solid (0.36 g, 56%).

4-(4-(Trifluoromethoxy)phenyl)-N-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrooxazol-2-amine(F17)

Isolated as a white solid (0.36 g, 56%).

4-(3-Chlorophenyl)-N-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrooxazol-2-amine(F18)

Isolated as a white solid (0.49 g, 73%).

4-(2-Chlorophenyl)-N-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrooxazol-2-amine(F19)

Isolated as a white solid (0.46 g, 69%).

(S)-4-Phenyl-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-5,6-dihydro-4H-1,3-oxazin-2-amine(F20)

Isolated as an off-white solid (0.075 g, 32%).

Example 8 General Procedure for the Preparation of 2-Amino Thiazolines

To a stirred solution of thiourea in tetrahydrofuran (5 vol) was addedcarbodiimidazole (1.5 eq). The reaction was stirred for 18 hours at roomtemperature. The reaction mixture was extracted with ethyl acetate,washed with water, and brine. The organic phase was dried over sodiumsulfate, filtered, and concentrated. The crude solid was recrystallizedusing ethyl acetate/petroleum ether or purified by flash columnchromatography to afford the title compound

The following compounds were prepared according to the proceduresdisclosed in Example 8:

4-(4-Methoxyphenyl)-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrothiazol-2-amine(F21)

Isolated as a white solid (0.46 g, 68%).

4-(p-Tolyl)-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrothiazol-2-amine(F22)

Isolated as a white solid (0.44 g, 66%).

4-(4-Fluorophenyl)-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrothiazol-2-amine(F24)

Isolated as a white solid (0.2 g, 41%).

4-(4-Chlorophenyl)-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrothiazol-2-amine(F25)

Isolated as a white solid (0.42 g, 63%).

4-(4-Bromophenyl)-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrothiazol-2-amine(F26)

Isolated as a white solid (0.16 g, 22%).

N-(4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4-(4-(trifluoromethyl)phenyl)-4,5-dihydrothiazol-2-amine(F27)

Isolated as a white solid (0.035 g, 5%).

4-(4-(Trifluoromethoxy)phenyl)-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrothiazol-2-amine(F28)

Isolated as a white solid (0.35 g, 56%).

4-(3-Chlorophenyl)-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrothiazol-2-amine(F29)

Isolated as a white solid (0.35 g, 47%).

4-(2-Chlorophenyl)-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrothiazol-2-amine(F30)

Isolated as a white solid (0.055 g, 8%).

4-(4-Chloro-3-methylphenyl)-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrothiazol-2-amine(F31)

Isolated as a white solid (0.25 g, 65%).

4-(4-Methoxyphenyl)-N-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrothiazol-2-amine(F32)

Isolated as a white solid (0.45 g, 66%).

4-(p-Tolyl)-N-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrothiazol-2-amine(F33)

Isolated as a white solid (0.39 g, 66%).

4-Phenyl-N-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrothiazol-2-amine(F34)

Isolated as a white solid (0.18 g, 28%).

4-(4-Fluorophenyl)-N-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrothiazol-2-amine(F35)

Isolated as a white solid (0.25 g, 37%).

4-(4-Chlorophenyl)-N-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrothiazol-2-amine(F36)

Isolated as a white solid (0.29 g, 43%).

4-(4-Chlorophenyl)-N-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrothiazol-2-amine(F37)

Isolated as a white solid (0.12 g, 16%).

4-(4-(Trifluoromethyl)phenyl)-N-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrothiazol-2-amine(F38)

Isolated as a white solid (0.14 g, 19%).

4-(4-(Trifluoromethoxy)phenyl)-N-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrothiazol-2-amine(F39)

Isolated as a white solid (0.44 g, 58%).

4-(3-Chlorophenyl)-N-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrothiazol-2-amine(F40)

Isolated as a white solid (0.17 g, 25%).

4-(2-Chlorophenyl)-N-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrothiazol-2-amine(F41)

Isolated as a white solid (0.062 g, 9%).

4-(4-Chloro-3-methylphenyl)-N-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrothiazol-2-amine(F42)

Isolated as a white solid (0.175 g, 70%).

Example 9 General Procedure for the Preparation of 2-Amino Oxazolinesand 2-Amino Oxazinanes

To a stirred solution of amino alcohol (1.0 eq) in dry tetrahydrofuran(20 vol) was added the appropriate isothiocyanate (1.0 eq) andtriethylamine (1.5 eq). The reaction mixture was heated at 50° C. for 12hours. The reaction mixture was concentrated under reduced pressure.Purification by flash column chromatography (silica gel) provided theintermediate thiourea. To a stirred solution of thiourea (1.0 eq) intetrahydrofuran (10 vol) was added a sodium hydroxide solution (2M, 2.5eq) and p-toluenesulfonyl chloride (1.1 eq) in tetrahydrofuran (5 vol).The reaction mixture was stirred at room temperature for 12 hours. Thereaction mixture was concentrated under reduced pressure and the residuewas diluted with water (20 mL) and extracted with ethyl acetate. Thecombined organic layers were washed with water, saturated brinesolution, dried over anhydrous sodium sulfate and concentrated underreduced pressure. Purification by flash column chromatography (silicagel) provided the title compounds.

The following compounds were prepared according to the proceduresdisclosed in Example 9:

4-Phenyl-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrooxazol-2-amine(F7)

The title compound was prepared with 2-amino-2-phenylethanol and3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazoleand isolated as a white solid (0.14 g, 30%).

4-(4-Chlorophenyl)-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-5,6-dihydro-4H-1,3-oxazin-2-amine(F43)

The title compound was prepared with3-amino-3-(4-chlorophenyl)propan-1-ol and3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazoleand isolated as an off-white solid (0.150 g, 64%).

4-(p-Tolyl)-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-5,6-dihydro-4H-1,3-oxazin-2-amine(F44)

The title compound was prepared with 3-amino-3-(p-tolyl)propan-1-ol and3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazoleand isolated as an off-white solid (0.020 g, 9%).

N-(4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4-(4-(trifluoromethyl)phenyl)-5,6-dihydro-4H-1,3-oxazin-2-amine(F45)

The title compound was prepared with3-amino-3-(4-(trifluoromethyl)phenyl)propan-1-ol and3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazoleand isolated as an off-white solid (0.10 g, 43%).

Example 10 General Procedure for the Preparation of 2-Amino Thiazolines

To a stirred solution of amino alcohol (1.0 eq) in dry tetrahydrofuran(20 vol) was added the appropriate isothiocyanate (1.0 eq) andtriethylamine (1.5 eq). The reaction mixture was heated at 50° C. for 12hours. The reaction mixture was concentrated under reduced pressure.Purification by flash column chromatography (silica gel) provided theintermediate thiourea. To a stirred solution of thiourea intetrahydrofuran (5 vol) was added carbodiimidazole (1.5 eq). Thereaction was stirred for 18 hours at room temperature. The reactionmixture was extracted with ethyl acetate, washed with water, and brine.The organic phase was dried over sodium sulfate, filtered, andconcentrated. The crude solid was recrystallized using ethylacetate/petroleum ether or purified by flash column chromatography toafford the title compound

The following compounds were prepared according to the proceduresdisclosed in Example 10:

4-Phenyl-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-4,5-dihydrothiazol-2-amine(F23)

Isolated as a white solid (0.23 g, 48%).

Example A Bioassays on Beet Armyworm (Spodoptera exigua, LAPHEG) (“BAW”)and Cabbage Looper (Trichoplusia ni, TRIPNI) (“CL”)

BAW has few effective parasites, diseases, or predators to lower itspopulation. BAW infests many weeds, trees, grasses, legumes, and fieldcrops. In various places, it is of economic concern upon asparagus,cotton, corn, soybeans, tobacco, alfalfa, sugar beets, peppers,tomatoes, potatoes, onions, peas, sunflowers, and citrus, among otherplants. The Cabbage Looper is a member of the moth family Noctuidae. Itis found throughout the world. It is attacks cabbage, cauliflower,broccoli, Brussel sprouts, tomatoes, cucumbers, potatoes, kale, turnips,mustard, peppers, eggplant, watermelons, melons, squash, cantaloupe,peas, beans, collards, lettuce, spinach, celery, parsley, beets, peas,alfalfa, soybeans, and cotton. This species is very destructive toplants due to its voracious consumption of leaves. In the case ofcabbage, however, they feed not only on the wrapper leaves, but also maybore into the developing head. The larvae consume three times theirweight in plant material daily. The feeding sites are marked by largeaccumulations of sticky, wet fecal material.

Consequently, because of the above factors control of these pests isimportant. Furthermore, molecules that control these pests (BAW and CL),which are known as chewing pests, are useful in controlling other peststhat chew on plants.

Certain molecules disclosed in this document were tested against BAW andCEW using procedures described in the following examples. In thereporting of the results, the “BAW & CL Rating Table” was used (SeeTable Section).

Bioassays on BAW

Bioassays on BAW were conducted using a 128-well diet tray assay. one tofive second instar BAW larvae were placed in each well (3 mL) of thediet tray that had been previously filled with 1 mL of artificial dietto which 50 μg/cm² of the test compound (dissolved in 50 μL of 90:10acetone-water mixture) had been applied (to each of eight wells) andthen allowed to dry. Trays were covered with a clear self-adhesive coverand held at 25° C., 14:10 light-dark for five to seven days. Percentmortality was recorded for the larvae in each well; activity in theeight wells was then averaged. The results are indicated in the tableentitled “Table ABC: Biological Results” (See Table Section).

Bioassays on Cabbage Looper in CL

Bioassays on CL were conducted using a 128-well diet tray assay, one tofive second instar CL larvae were placed in each well (3 mL) of the diettray that had been previously filled with 1 mL of artificial diet towhich 50 μg/cm² of the test compound (dissolved in 50 μL of 90:10acetone-water mixture) had been applied (to each of eight wells) andthen allowed to dry. Trays were covered with a clear self-adhesive coverand held at 25° C., 14:10 light-dark for five to seven days. Percentmortality was recorded for the larvae in each well; activity in theeight wells was then averaged. The results are indicated in the tableentitled “Table ABC: Biological Results” (See Table Section).

Example B Bioassays on Green Peach Aphid (Myzus persicae, MYZUPE)(“GPA”)

GPA is the most significant aphid pest of peach trees, causing decreasedgrowth, shriveling of the leaves, and the death of various tissues. Itis also hazardous because it acts as a vector for the transport of plantviruses, such as potato virus Y and potato leafroll virus to members ofthe nightshade/potato family Solanaceae, and various mosaic viruses tomany other food crops. GPA attacks such plants as broccoli, burdock,cabbage, carrot, cauliflower, daikon, eggplant, green beans, lettuce,macadamia, papaya, peppers, sweet potatoes, tomatoes, watercress, andzucchini, among other plants. GPA also attacks many ornamental cropssuch as carnation, chrysanthemum, flowering white cabbage, poinsettia,and roses. GPA has developed resistance to many pesticides.Consequently, because of the above factors control of this pest isimportant. Furthermore, molecules that control this pest (GPA), which isknown as a sucking pest, are useful in controlling other pests that suckon plants.

Certain molecules disclosed in this document were tested against GPAusing procedures described in the following example. In the reporting ofthe results, the “GPA Rating Table” was used (See Table Section).

Cabbage seedlings grown in 3-inch pots, with 2-3 small (3-5 cm) trueleaves, were used as test substrate. The seedlings were infested with20-50 GPA (wingless adult and nymph stages) one day prior to chemicalapplication. Four pots with individual seedlings were used for eachtreatment. Test compounds (2 mg) were dissolved in 2 mL ofacetone/methanol (1:1) solvent, forming stock solutions of 1000 ppm testcompound. The stock solutions were diluted 5× with 0.025% Tween 20 inwater to obtain the solution at 200 ppm test compound. A hand-heldaspirator-type sprayer was used for spraying a solution to both sides ofcabbage leaves until runoff. Reference plants (solvent check) weresprayed with the diluent only containing 20% by volume ofacetone/methanol (1:1) solvent. Treated plants were held in a holdingroom for three days at approximately 25° C. and ambient relativehumidity (RH) prior to grading. Evaluation was conducted by counting thenumber of live aphids per plant under a microscope. Percent Control wasmeasured by using Abbott's correction formula (W. S. Abbott, “A Methodof Computing the Effectiveness of an Insecticide” J. Econ. Entomol. 18(1925), pp. 265-267) as follows. Corrected % Control=100*(X−Y)/X whereX=No. of live aphids on solvent check plants and Y=No. of live aphids ontreated plants

The results are indicated in the table entitled “Table ABC: BiologicalResults” (See Table Section).

Example C Bioassays on Yellow Fever Mosquito (Aedes aegypti, AEDSAE)(“YFM”)

YFM prefers to feed on humans during the daytime and is most frequentlyfound in or near human habitations. YFM is a vector for transmittingseveral diseases. It is a mosquito that can spread the dengue fever andyellow fever viruses. Yellow fever is the second most dangerousmosquito-borne disease after malaria. Yellow fever is an acute viralhemorrhagic disease and up to 50% of severely affected persons withouttreatment will die from yellow fever. There are an estimated 200,000cases of yellow fever, causing 30,000 deaths, worldwide each year.Dengue fever is a nasty, viral disease; it is sometimes called“breakbone fever” or “break-heart fever” because of the intense pain itcan produce. Dengue fever kills about 20,000 people annually.Consequently, because of the above factors control of this pest isimportant. Furthermore, molecules that control this pest (YFM), which isknown as a sucking pest, are useful in controlling other pests thatcause human and animal suffering.

Certain molecules disclosed in this document were tested against YFMusing procedures described in the following paragraph. In the reportingof the results, the “YFM Rating Table” was used (See Table Section).

Master plates containing 400 μg of a molecule dissolved in 100 μL ofdimethyl sulfoxide (DMSO) (equivalent to a 4000 ppm solution) are used.A master plate of assembled molecules contains 15 μL per well. To thisplate, 135 μL of a 90:10 water:acetone mixture is added to each well. Arobot (Biomek® NXP Laboratory Automation Workstation) is programmed todispense 15 μL aspirations from the master plate into an empty 96-wellshallow plate (“daughter” plate). There are 6 reps (“daughter” plates)created per master. The created daughter plates are then immediatelyinfested with YFM larvae.

The day before plates are to be treated, mosquito eggs are placed inMillipore water containing liver powder to begin hatching (4 g. into 400mL). After the daughter plates are created using the robot, they areinfested with 220 μL of the liver powder/larval mosquito mixture (about1 day-old larvae). After plates are infested with mosquito larvae, anon-evaporative lid is used to cover the plate to reduce drying. Platesare held at room temperature for 3 days prior to grading. After 3 days,each well is observed and scored based on mortality.

The results are indicated in the table entitled “Table ABC: BiologicalResults” (See Table Section).

Agriculturally Acceptable Acid Addition Salts, Salt Derivatives,Solvates, Ester Derivatives, Polymorphs, Isotopes, and Radionuclides

Molecules of Formula One may be formulated into agriculturallyacceptable acid addition salts. By way of a non-limiting example, anamine function can form salts with hydrochloric, hydrobromic, sulfuric,phosphoric, acetic, benzoic, citric, malonic, salicylic, malic, fumaric,oxalic, succinic, tartaric, lactic, gluconic, ascorbic, maleic,aspartic, benzenesulfonic, methanesulfonic, ethanesulfonic,hydroxyl-methanesulfonic, and hydroxyethanesulfonic acids. Additionally,by way of a non-limiting example, an acid function can form saltsincluding those derived from alkali or alkaline earth metals and thosederived from ammonia and amines. Examples of preferred cations includesodium, potassium, and magnesium.

Molecules of Formula One may be formulated into salt derivatives. By wayof a non-limiting example, a salt derivative can be prepared bycontacting a free base with a sufficient amount of the desired acid toproduce a salt. A free base may be regenerated by treating the salt witha suitable dilute aqueous base solution such as dilute aqueous sodiumhydroxide, potassium carbonate, ammonia, and sodium bicarbonate. As anexample, in many cases, a pesticide, such as 2,4-D, is made morewater-soluble by converting it to its dimethylamine salt.

Molecules of Formula One may be formulated into stable complexes with asolvent, such that the complex remains intact after the non-complexedsolvent is removed. These complexes are often referred to as “solvates.”However, it is particularly desirable to form stable hydrates with wateras the solvent.

Molecules of Formula One may be made into ester derivatives. These esterderivatives can then be applied in the same manner as the moleculesdisclosed in this document is applied.

Molecules of Formula One may be made as various crystal polymorphs.Polymorphism is important in the development of agrochemicals sincedifferent crystal polymorphs or structures of the same molecule can havevastly different physical properties and biological performances.

Molecules of Formula One may be made with different isotopes. Ofparticular importance are molecules having ²H (also known as deuterium)in place of ¹H.

Molecules of Formula One may be made with different radionuclides. Ofparticular importance are molecules having ¹⁴C.

Stereoisomers

Molecules of Formula One may exist as one or more stereoisomers. Thus,certain molecules can be produced as racemic mixtures. It will beappreciated by those skilled in the art that one stereoisomer may bemore active than the other stereoisomers. Individual stereoisomers maybe obtained by known selective synthetic procedures, by conventionalsynthetic procedures using resolved starting materials, or byconventional resolution procedures. Certain molecules disclosed in thisdocument can exist as two or more isomers. The various isomers includegeometric isomers, diastereomers, and enantiomers. Thus, the moleculesdisclosed in this document include geometric isomers, racemic mixtures,individual stereoisomers, and optically active mixtures. It will beappreciated by those skilled in the art that one isomer may be moreactive than the others. The structures disclosed in the presentdisclosure are drawn in only one geometric form for clarity, but areintended to represent all geometric forms of the molecule.

Combinations

In another embodiment, molecules of Formula One may be used incombination (such as, in a compositional mixture, or a simultaneous orsequential application) with one or more compounds each having a mode ofaction that is the same as, similar to, or different from, the mode ofaction (“MOA”) of the molecules of Formula One. Modes of action include,for example the following: Acetylcholinesterase (AChE) inhibitors;GABA-gated chloride channel antagonists; Sodium channel modulators;Nicotinic acetylcholine (nAChR) agonists; Nicotinic acetylcholinereceptor (nAChR) allosteric activators; Chloride channel activators;Juvenile hormone mimics; Miscellaneous non-specific (multi-site)inhibitors; Selective homopteran feeding blockers; Mite growthinhibitors; Microbial disruptors of insect midgut membranes; Inhibitorsof mitochondrial ATP synthase; Uncouplers of oxidative phosphorylationvia disruption of the proton gradient; Nicotinic acetylcholine receptor(nAChR) channel blockers; Inhibitors of chitin biosynthesis, type 0;Inhibitors of chitin biosynthesis, type 1; Moulting disruptor, Dipteran;Ecdysone receptor agonists; Octopamine receptor agonists; Mitochondrialcomplex III electron transport inhibitors; Mitochondrial complex Ielectron transport inhibitors; Voltage-dependent sodium channelblockers; Inhibitors of acetyl CoA carboxylase; Mitochondrial complex IVelectron transport inhibitors; Mitochondrial complex II electrontransport inhibitors; and Ryanodine receptor modulators.

In another embodiment, molecules of Formula One may be used incombination (such as, in a compositional mixture, or a simultaneous orsequential application) with one or more compounds having acaricidal,algicidal, avicidal, bactericidal, fungicidal, herbicidal, insecticidal,molluscicidal, nematicidal, rodenticidal, and/or virucidal properties.

In another embodiment, the molecules of Formula One may be used incombination (such as, in a compositional mixture, or a simultaneous orsequential application) with one or more compounds that areantifeedants, bird repellents, chemosterilants, herbicide safeners,insect attractants, insect repellents, mammal repellents, matingdisrupters, plant activators, plant growth regulators, and/orsynergists.

In another embodiment, the molecules of Formula One may be used incombination (such as, in a compositional mixture, or a simultaneous orsequential application) with “another compound”, such as one or more ofthe following compounds—(3-ethoxypropyl)mercury bromide,1,2-dichloropropane, 1,3-dichloropropene, 1-methylcyclopropene,1-naphthol, 2-(octylthio)ethanol, 2,3,5-tri-iodobenzoic acid, 2,3,6-TBA,2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA-potassium,2,3,6-TBA-sodium, 2,4,5-T, 2,4,5-T-2-butoxypropyl, 2,4,5-T-2-ethylhexyl,2,4,5-T-3-butoxypropyl, 2,4,5-TB, 2,4,5-T-butometyl, 2,4,5-T-butotyl,2,4,5-T-butyl, 2,4,5-T-isobutyl, 2,4,5-T-isoctyl, 2,4,5-T-isopropyl,2,4,5-T-methyl, 2,4,5-T-pentyl, 2,4,5-T-sodium,2,4,5-T-triethylammonium, 2,4,5-T-trolamine, 2,4-D,2,4-D-2-butoxypropyl, 2,4-D-2-ethylhexyl, 2,4-D-3-butoxypropyl,2,4-D-ammonium, 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethylammonium,2,4-DB-isoctyl, 2,4-DB-potassium, 2,4-DB-sodium, 2,4-D-butotyl,2,4-D-butyl, 2,4-D-diethylammonium, 2,4-D-dimethylammonium,2,4-D-diolamine, 2,4-D-dodecylammonium, 2,4-DEB, 2,4-DEP, 2,4-D-ethyl,2,4-D-heptylammonium, 2,4-D-isobutyl, 2,4-D-isoctyl, 2,4-D-isopropyl,2,4-D-isopropylammonium, 2,4-D-lithium, 2,4-D-meptyl, 2,4-D-methyl,2,4-D-octyl, 2,4-D-pentyl, 2,4-D-potassium, 2,4-D-propyl, 2,4-D-sodium,2,4-D-tefuryl, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium,2,4-D-tris(2-hydroxypropyl)ammonium, 2,4-D-trolamine, 2iP,2-methoxyethylmercury chloride, 2-phenylphenol, 3,4-DA, 3,4-DB, 3,4-DP,4-aminopyridine, 4-CPA, 4-CPA-diolamine, 4-CPA-potassium, 4-CPA-sodium,4-CPB, 4-CPP, 4-hydroxyphenethyl alcohol, 8-hydroxyquinoline sulfate,8-phenylmercurioxyquinoline, abamectin, abscisic acid, ACC, acephate,acequinocyl, acetamiprid, acethion, acetochlor, acetophos, acetoprole,acibenzolar, acibenzolar-S-methyl, acifluorfen, acifluorfen-methyl,acifluorfen-sodium, aclonifen, acrep, acrinathrin, acrolein,acrylonitrile, acypetacs, acypetacs-copper, acypetacs-zinc,afidopyropen, afoxolaner, alachlor, alanycarb, albendazole, aldicarb,aldimorph, aldoxycarb, aldrin, allethrin, allicin, allidochlor,allosamidin, alloxydim, alloxydim-sodium, allyl alcohol, allyxycarb,alorac, alpha-cypermethrin, alpha-endosulfan, ametoctradin, ametridione,ametryn, amibuzin, amicarbazone, amicarthiazol, amidithion, amidoflumet,amidosulfuron, aminocarb, aminocyclopyrachlor,aminocyclopyrachlor-methyl, aminocyclopyrachlor-potassium, aminopyralid,aminopyralid-potassium, aminopyralid-tris(2-hydroxypropyl)ammonium,amiprofos-methyl, amiprophos, amisulbrom, amiton, amiton oxalate,amitraz, amitrole, ammonium sulfamate, ammonium α-naphthaleneacetate,amobam, ampropylfos, anabasine, anabasine sulfate, ancymidol, anilazine,anilofos, anisuron, anthraquinone, antu, apholate, aramite, arsenousoxide, asomate, aspirin, asulam, asulam-potassium, asulam-sodium,athidathion, atraton, atrazine, aureofungin, aviglycine, aviglycinehydrochloride, azaconazole, azadirachtin, azafenidin, azamethiphos,azimsulfuron, azinphos-ethyl, azinphos-methyl, aziprotryne, azithiram,azobenzene, azocyclotin, azothoate, azoxystrobin, bachmedesh, barban,barium hexafluorosilicate, barium polysulfide, barthrin, BCPC,beflubutamid, benalaxyl, benalaxyl-M, benazolin,benazolin-dimethylammonium, benazolin-ethyl, benazolin-potassium,bencarbazone, benclothiaz, bendiocarb, benfluralin, benfuracarb,benfuresate, benodanil, benomyl, benoxacor, benoxafos, benquinox,bensulfuron, bensulfuron-methyl, bensulide, bensultap, bentaluron,bentazone, bentazone-sodium, benthiavalicarb, benthiavalicarb-isopropyl,benthiazole, bentranil, benzadox, benzadox-ammonium, benzalkoniumchloride, benzamacril, benzamacril-isobutyl, benzamorf, benzfendizone,benzipram, benzobicyclon, benzofenap, benzofluor, benzohydroxamic acid,benzovindiflupyr, benzoximate, benzoylprop, benzoylprop-ethyl,benzthiazuron, benzyl benzoate, benzyladenine, berberine, berberinechloride, beta-cyfluthrin, beta-cypermethrin, bethoxazin, bicyclopyrone,bifenazate, bifenox, bifenthrin, bifujunzhi, bilanafos,bilanafos-sodium, binapacryl, bingqingxiao, bioallethrin,bioethanomethrin, biopermethrin, bioresmethrin, biphenyl, bisazir,bismerthiazol, bispyribac, bispyribac-sodium, bistrifluron, bitertanol,bithionol, bixafen, blasticidin-S, borax, Bordeaux mixture, boric acid,boscalid, brassinolide, brassinolide-ethyl, brevicomin, brodifacoum,brofenvalerate, brofluthrinate, bromacil, bromacil-lithium,bromacil-sodium, bromadiolone, bromethalin, bromethrin, bromfenvinfos,bromoacetamide, bromobonil, bromobutide, bromocyclen, bromo-DDT,bromofenoxim, bromophos, bromophos-ethyl, bromopropylate, bromothalonil,bromoxynil, bromoxynil butyrate, bromoxynil heptanoate, bromoxyniloctanoate, bromoxynil-potassium, brompyrazon, bromuconazole, bronopol,bucarpolate, bufencarb, buminafos, bupirimate, buprofezin, Burgundymixture, busulfan, butacarb, butachlor, butafenacil, butamifos,butathiofos, butenachlor, butethrin, buthidazole, buthiobate, buthiuron,butocarboxim, butonate, butopyronoxyl, butoxycarboxim, butralin,butroxydim, buturon, butylamine, butylate, cacodylic acid, cadusafos,cafenstrole, calcium arsenate, calcium chlorate, calcium cyanamide,calcium polysulfide, calvinphos, cambendichlor, camphechlor, camphor,captafol, captan, carbamorph, carbanolate, carbaryl, carbasulam,carbendazim, carbendazim benzenesulfonate, carbendazim sulfite,carbetamide, carbofuran, carbon disulfide, carbon tetrachloride,carbophenothion, carbosulfan, carboxazole, carboxide, carboxin,carfentrazone, carfentrazone-ethyl, carpropamid, cartap, cartaphydrochloride, carvacrol, carvone, CDEA, cellocidin, CEPC, ceralure,Cheshunt mixture, chinomethionat, chitosan, chlobenthiazone,chlomethoxyfen, chloralose, chloramben, chloramben-ammonium,chloramben-diolamine, chloramben-methyl, chloramben-methylammonium,chloramben-sodium, chloramine phosphorus, chloramphenicol,chloraniformethan, chloranil, chloranocryl, chlorantraniliprole,chlorazifop, chlorazifop-propargyl, chlorazine, chlorbenside,chlorbenzuron, chlorbicyclen, chlorbromuron, chlorbufam, chlordane,chlordecone, chlordimeform, chlordimeform hydrochloride,chlorempenthrin, chlorethoxyfos, chloreturon, chlorfenac,chlorfenac-ammonium, chlorfenac-sodium, chlorfenapyr, chlorfenazole,chlorfenethol, chlorfenprop, chlorfenson, chlorfensulphide,chlorfenvinphos, chlorfluazuron, chlorflurazole, chlorfluren,chlorfluren-methyl, chlorflurenol, chlorflurenol-methyl, chloridazon,chlorimuron, chlorimuron-ethyl, chlormephos, chlormequat, chlormequatchloride, chlornidine, chlornitrofen, chlorobenzilate,chlorodinitronaphthalenes, chloroform, chloromebuform, chloromethiuron,chloroneb, chlorophacinone, chlorophacinone-sodium, chloropicrin,chloropon, chloropropylate, chlorothalonil, chlorotoluron, chloroxuron,chloroxynil, chlorphonium, chlorphonium chloride, chlorphoxim,chlorprazophos, chlorprocarb, chlorpropham, chlorpyrifos,chlorpyrifos-methyl, chlorquinox, chlorsulfuron, chlorthal,chlorthal-dimethyl, chlorthal-monomethyl, chlorthiamid, chlorthiophos,chlozolinate, choline chloride, cholecalciferol, chromafenozide, cinerinI, cinerin II, cinerins, cinidon-ethyl, cinmethylin, cinosulfuron,ciobutide, cisanilide, cismethrin, clacyfos, clethodim, climbazole,cliodinate, clodinafop, clodinafop-propargyl, cloethocarb, clofencet,clofencet-potassium, clofentezine, clofibric acid, clofop,clofop-isobutyl, clomazone, clomeprop, cloprop, cloproxydim, clopyralid,clopyralid-methyl, clopyralid-olamine, clopyralid-potassium,clopyralid-tris(2-hydroxypropyl)ammonium, cloquintocet,cloquintocet-mexyl, cloransulam, cloransulam-methyl, closantel,clothianidin, clotrimazole, cloxyfonac, cloxyfonac-sodium, CMA,codlelure, colophonate, copper acetate, copper acetoarsenite, copperarsenate, copper carbonate, basic, copper hydroxide, copper naphthenate,copper oleate, copper oxychloride, copper silicate, copper sulfate,copper zinc chromate, coumachlor, coumafuryl, coumaphos, coumatetralyl,coumithoate, coumoxystrobin, coumoxystrobin, CPMC, CPMF, CPPC,credazine, cresol, crimidine, crotamiton, crotoxyphos, crufomate,cryolite, cue-lure, cufraneb, cumyluron, cuprobam, cuprous oxide,curcumenol, cyanamide, cyanatryn, cyanazine, cyanofenphos, cyanophos,cyanthoate, cyantraniliprole, cyazofamid, cybutryne, cyclafuramid,cyclanilide, cyclaniliprole, cyclethrin, cycloate, cycloheximide,cycloprate, cycloprothrin, cyclopyrimorate, cyclosulfamuron,cycloxaprid, cycloxydim, cycluron, cyenopyrafen, cyflufenamid,cyflumetofen, cyfluthrin, cyhalofop, cyhalofop-butyl, cyhalothrin,cyhexatin, cymiazole, cymiazole hydrochloride, cymoxanil, cyometrinil,cypendazole, cypermethrin, cyperquat, cyperquat chloride, cyphenothrin,cyprazine, cyprazole, cyproconazole, cyprodinil, cyprofuram, cypromid,cyprosulfamide, cyromazine, cythioate, daimuron, dalapon,dalapon-calcium, dalapon-magnesium, dalapon-sodium, daminozide,dayoutong, dazomet, dazomet-sodium, DBCP, d-camphor, DCIP, DCPTA, DDT,debacarb, decafentin, decarbofuran, dehydroacetic acid, delachlor,deltamethrin, demephion, demephion-O, demephion-S, demeton,demeton-methyl, demeton-O, demeton-O-methyl, demeton-S,demeton-S-methyl, demeton-S-methylsulphon, desmedipham, desmetryn,d-fanshiluquebingjuzhi, diafenthiuron, dialifos, di-allate, diamidafos,diatomaceous earth, diazinon, dibutyl phthalate, dibutyl succinate,dicamba, dicamba-diglycolamine, dicamba-dimethylammonium,dicamba-diolamine, dicamba-isopropylammonium, dicamba-methyl,dicamba-olamine, dicamba-potassium, dicamba-sodium, dicamba-trolamine,dicapthon, dichlobenil, dichlofenthion, dichlofluanid, dichlone,dichloralurea, dichlorbenzuron, dichlorflurenol, dichlorflurenol-methyl,dichlormate, dichlormid, dichlorophen, dichlorprop,dichlorprop-2-ethylhexyl, dichlorprop-butotyl,dichlorprop-dimethylammonium, dichlorprop-ethylammonium,dichlorprop-isoctyl, dichlorprop-methyl, dichlorprop-P,dichlorprop-P-2-ethylhexyl, dichlorprop-P-dimethylammonium,dichlorprop-potassium, dichlorprop-P-potassium, dichlorprop-P-sodium,dichlorprop-sodium, dichlorvos, dichlozoline, diclobutrazol, diclocymet,diclofop, diclofop-methyl, diclomezine, diclomezine-sodium, dicloran,diclosulam, dicofol, dicoumarol, dicresyl, dicrotophos, dicyclanil,dicyclonon, dieldrin, dienochlor, diethamquat, diethamquat dichloride,diethatyl, diethatyl-ethyl, diethofencarb, dietholate, diethylpyrocarbonate, diethyltoluamide, difenacoum, difenoconazole,difenopenten, difenopenten-ethyl, difenoxuron, difenzoquat, difenzoquatmetilsulfate, difethialone, diflovidazin, diflubenzuron, diflufenican,diflufenzopyr, diflufenzopyr-sodium, diflumetorim, dikegulac,dikegulac-sodium, dilor, dimatif, dimefluthrin, dimefox, dimefuron,dimepiperate, dimetachlone, dimetan, dimethacarb, dimethachlor,dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimethirimol,dimethoate, dimethomorph, dimethrin, dimethyl carbate, dimethylphthalate, dimethylvinphos, dimetilan, dimexano, dimidazon,dimoxystrobin, dinex, dinex-diclexine, dingjunezuo, diniconazole,diniconazole-M, dinitramine, dinobuton, dinocap, dinocap-4, dinocap-6,dinocton, dinofenate, dinopenton, dinoprop, dinosam, dinoseb, dinosebacetate, dinoseb-ammonium, dinoseb-diolamine, dinoseb-sodium,dinoseb-trolamine, dinosulfon, dinotefuran, dinoterb, dinoterb acetate,dinoterbon, diofenolan, dioxabenzofos, dioxacarb, dioxathion,diphacinone, diphacinone-sodium, diphenamid, diphenyl sulfone,diphenylamine, dipropalin, dipropetryn, dipyrithione, diquat, diquatdibromide, disparlure, disul, disulfiram, disulfoton, disul-sodium,ditalimfos, dithianon, dithicrofos, dithioether, dithiopyr, diuron,d-limonene, DMPA, DNOC, DNOC-ammonium, DNOC-potassium, DNOC-sodium,dodemorph, dodemorph acetate, dodemorph benzoate, dodicin, dodicinhydrochloride, dodicin-sodium, dodine, dofenapyn, dominicalure,doramectin, drazoxolon, DSMA, dufulin, EBEP, EBP, ecdysterone,edifenphos, eglinazine, eglinazine-ethyl, emamectin, emamectin benzoate,EMPC, empenthrin, endosulfan, endothal, endothal-diammonium,endothal-dipotassium, endothal-disodium, endothion, endrin,enestroburin, enoxastrobin, EPN, epocholeone, epofenonane,epoxiconazole, eprinomectin, epronaz, EPTC, erbon, ergocalciferol,erlujixiancaoan, esdepallethrine, esfenvalerate, esprocarb, etacelasil,etaconazole, etaphos, etem, ethaboxam, ethachlor, ethalfluralin,ethametsulfuron, ethametsulfuron-methyl, ethaprochlor, ethephon,ethidimuron, ethiofencarb, ethiolate, ethion, ethiozin, ethiprole,ethirimol, ethoate-methyl, ethofumesate, ethohexadiol, ethoprophos,ethoxyfen, ethoxyfen-ethyl, ethoxyquin, ethoxysulfuron, ethychlozate,ethyl formate, ethyl α-naphthaleneacetate, ethyl-DDD, ethylene, ethylenedibromide, ethylene dichloride, ethylene oxide, ethylicin, ethylmercury2,3-dihydroxypropyl mercaptide, ethylmercury acetate, ethylmercurybromide, ethylmercury chloride, ethylmercury phosphate, etinofen,etnipromid, etobenzanid, etofenprox, etoxazole, etridiazole, etrimfos,eugenol, EXD, famoxadone, famphur, fenamidone, fenaminosulf,fenaminstrobin, fenamiphos, fenapanil, fenarimol, fenasulam, fenazaflor,fenazaquin, fenbuconazole, fenbutatin oxide, fenchlorazole,fenchlorazole-ethyl, fenchlorphos, fenclorim, fenethacarb, fenfluthrin,fenfuram, fenhexamid, fenitropan, fenitrothion, fenjuntong, fenobucarb,fenoprop, fenoprop-3-butoxypropyl, fenoprop-butometyl, fenoprop-butotyl,fenoprop-butyl, fenoprop-isoctyl, fenoprop-methyl, fenoprop-potassium,fenothiocarb, fenoxacrim, fenoxanil, fenoxaprop, fenoxaprop-ethyl,fenoxaprop-P, fenoxaprop-P-ethyl, fenoxasulfone, fenoxycarb,fenpiclonil, fenpirithrin, fenpropathrin, fenpropidin, fenpropimorph,fenpyrazamine, fenpyroximate, fenquinotrione, fenridazon,fenridazon-potassium, fenridazon-propyl, fenson, fensulfothion,fenteracol, fenthiaprop, fenthiaprop-ethyl, fenthion, fenthion-ethyl,fentin, fentin acetate, fentin chloride, fentin hydroxide, fentrazamide,fentrifanil, fenuron, fenuron TCA, fenvalerate, ferbam, ferimzone,ferrous sulfate, fipronil, flamprop, flamprop-isopropyl, flamprop-M,flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron,flocoumafen, flometoquin, flonicamid, florasulam, fluacrypyrim,fluazifop, fluazifop-butyl, fluazifop-methyl, fluazifop-P,fluazifop-P-butyl, fluazinam, fluazolate, fluazuron, flubendiamide,flubenzimine, flucarbazone, flucarbazone-sodium, flucetosulfuron,fluchloralin, flucofuron, flucycloxuron, flucythrinate, fludioxonil,fluenetil, fluensulfone, flufenacet, flufenerim, flufenican,flufenoxuron, flufenoxystrobin, flufenprox, flufenpyr, flufenpyr-ethyl,flufiprole, fluhexafon, flumethrin, flumetover, flumetralin,flumetsulam, flumezin, flumiclorac, flumiclorac-pentyl, flumioxazin,flumipropyn, flumorph, fluometuron, fluopicolide, fluopyram,fluorbenside, fluoridamid, fluoroacetamide, fluorodifen, fluoroglycofen,fluoroglycofen-ethyl, fluoroimide, fluoromidine, fluoronitrofen,fluothiuron, fluotrimazole, fluoxastrobin, flupoxam, flupropacil,flupropadine, flupropanate, flupropanate-sodium, flupyradifurone,flupyrsulfuron, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium,fluquinconazole, fluralaner, flurazole, flurenol, flurenol-butyl,flurenol-methyl, fluridone, flurochloridone, fluroxypyr,fluroxypyr-butometyl, fluroxypyr-meptyl, flurprimidol, flursulamid,flurtamone, flusilazole, flusulfamide, fluthiacet, fluthiacet-methyl,flutianil, flutolanil, flutriafol, fluvalinate, fluxapyroxad,fluxofenim, folpet, fomesafen, fomesafen-sodium, fonofos, foramsulfuron,forchlorfenuron, formaldehyde, formetanate, formetanate hydrochloride,formothion, formparanate, formparanate hydrochloride, fosamine,fosamine-ammonium, fosetyl, fosetyl-aluminium, fosmethilan, fospirate,fosthiazate, fosthietan, frontalin, fuberidazole, fucaojing, fucaomi,funaihecaoling, fuphenthiourea, furalane, furalaxyl, furamethrin,furametpyr, furathiocarb, furcarbanil, furconazole, furconazole-cis,furethrin, furfural, furilazole, furmecyclox, furophanate, furyloxyfen,gamma-cyhalothrin, gamma-HCH, genit, gibberellic acid, gibberellins,gliftor, glufosinate, glufosinate-ammonium, glufosinate-P,glufosinate-P-ammonium, glufosinate-P-sodium, glyodin, glyoxime,glyphosate, glyphosate-diammonium, glyphosate-dimethylammonium,glyphosate-isopropylammonium, glyphosate-monoammonium,glyphosate-potassium, glyphosate-sesquisodium, glyphosate-trimesium,glyphosine, gossyplure, grandlure, griseofulvin, guazatine, guazatineacetates, halacrinate, halauxifen, halauxifen-methyl, halfenprox,halofenozide, halosafen, halosulfuron, halosulfuron-methyl, haloxydine,haloxyfop, haloxyfop-etotyl, haloxyfop-methyl, haloxyfop-P,haloxyfop-P-etotyl, haloxyfop-P-methyl, haloxyfop-sodium, HCH, hemel,hempa, HEOD, heptachlor, heptafluthrin, heptenophos, heptopargil,herbimycin, heterophos, hexachloroacetone, hexachlorobenzene,hexachlorobutadiene, hexachlorophene, hexaconazole, hexaflumuron,hexaflurate, hexalure, hexamide, hexazinone, hexylthiofos, hexythiazox,HHDN, holosulf, huancaiwo, huangcaoling, huanjunzuo, hydramethylnon,hydrargaphen, hydrated lime, hydrogen cyanide, hydroprene, hymexazol,hyquincarb, IAA, IBA, icaridin, imazalil, imazalil nitrate, imazalilsulfate, imazamethabenz, imazamethabenz-methyl, imazamox,imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr,imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium,imazaquin-methyl, imazaquin-sodium, imazethapyr, imazethapyr-ammonium,imazosulfuron, imibenconazole, imicyafos, imidacloprid, imidaclothiz,iminoctadine, iminoctadine triacetate, iminoctadine trialbesilate,imiprothrin, inabenfide, indanofan, indaziflam, indoxacarb, inezin,iodobonil, iodocarb, iodomethane, iodosulfuron, iodosulfuron-methyl,iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium,ioxynil, ioxynil octanoate, ioxynil-lithium, ioxynil-sodium, ipazine,ipconazole, ipfencarbazone, iprobenfos, iprodione, iprovalicarb,iprymidam, ipsdienol, ipsenol, IPSP, isamidofos, isazofos, isobenzan,isocarbamid, isocarbophos, isocil, isodrin, isofenphos,isofenphos-methyl, isofetamid, isolan, isomethiozin, isonoruron,isopolinate, isoprocarb, isopropalin, isoprothiolane, isoproturon,isopyrazam, isopyrimol, isothioate, isotianil, isouron, isovaledione,isoxaben, isoxachlortole, isoxadifen, isoxadifen-ethyl, isoxaflutole,isoxapyrifop, isoxathion, ivermectin, izopamfos, japonilure, japothrins,jasmolin I, jasmolin II, jasmonic acid, jiahuangchongzong,jiajizengxiaolin, jiaxiangjunzhi, jiecaowan, jiecaoxi, jodfenphos,juvenile hormone I, juvenile hormone II, juvenile hormone III,kadethrin, karbutilate, karetazan, karetazan-potassium, kasugamycin,kasugamycin hydrochloride, kejunlin, kelevan, ketospiradox,ketospiradox-potassium, kinetin, kinoprene, kresoxim-methyl, kuicaoxi,lactofen, lambda-cyhalothrin, latilure, lead arsenate, lenacil,lepimectin, leptophos, lindane, lineatin, linuron, lirimfos, litlure,looplure, lufenuron, lvdingjunzhi, Ivxiancaolin, lythidathion, MAA,malathion, maleic hydrazide, malonoben, maltodextrin, MAMA, mancopper,mancozeb, mandipropamid, mandestrobin, maneb, matrine, mazidox, MCPA,MCPA-2-ethylhexyl, MCPA-butotyl, MCPA-butyl, MCPA-dimethylammonium,MCPA-diolamine, MCPA-ethyl, MCPA-isobutyl, MCPA-isoctyl, MCPA-isopropyl,MCPA-methyl, MCPA-olamine, MCPA-potassium, MCPA-sodium, MCPA-thioethyl,MCPA-trolamine, MCPB, MCPB-ethyl, MCPB-methyl, MCPB-sodium, mebenil,mecarbam, mecarbinzid, mecarphon, mecoprop, mecoprop-2-ethylhexyl,mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl,mecoprop-isoctyl, mecoprop-methyl, mecoprop-P, mecoprop-P-2-ethylhexyl,mecoprop-P-dimethylammonium, mecoprop-P-isobutyl, mecoprop-potassium,mecoprop-P-potassium, mecoprop-sodium, mecoprop-trolamine, medimeform,medinoterb, medinoterb acetate, medlure, mefenacet, mefenpyr,mefenpyr-diethyl, mefluidide, mefluidide-diolamine,mefluidide-potassium, megatomoic acid, menazon, mepanipyrim,meperfluthrin, mephenate, mephosfolan, mepiquat, mepiquat chloride,mepiquat pentaborate, mepronil, meptyldinocap, mercuric chloride,mercuric oxide, mercurous chloride, merphos, mesoprazine, mesosulfuron,mesosulfuron-methyl, mesotrione, mesulfen, mesulfenfos, metaflumizone,metalaxyl, metalaxyl-M, metaldehyde, metam, metam-ammonium, metamifop,metamitron, metam-potassium, metam-sodium, metazachlor, metazosulfuron,metazoxolon, metconazole, metepa, metflurazon, methabenzthiazuron,methacrifos, methalpropalin, methamidophos, methasulfocarb, methazole,methfuroxam, methidathion, methiobencarb, methiocarb,methiopyrisulfuron, methiotepa, methiozolin, methiuron, methocrotophos,methometon, methomyl, methoprene, methoprotryne, methoquin-butyl,methothrin, methoxychlor, methoxyfenozide, methoxyphenone, methylapholate, methyl bromide, methyl eugenol, methyl iodide, methylisothiocyanate, methylacetophos, methylchloroform, methyldymron,methylene chloride, methylmercury benzoate, methylmercury dicyandiamide,methylmercury pentachlorophenoxide, methylneodecanamide, metiram,metobenzuron, metobromuron, metofluthrin, metolachlor, metolcarb,metominostrobin, metosulam, metoxadiazone, metoxuron, metrafenone,metribuzin, metsulfovax, metsulfuron, metsulfuron-methyl, mevinphos,mexacarbate, mieshuan, milbemectin, milbemycin oxime, milneb, mipafox,mirex, MNAF, moguchun, molinate, molosultap, momfluorothrin, monalide,monisouron, monochloroacetic acid, monocrotophos, monolinuron,monosulfuron, monosulfuron-ester, monuron, monuron TCA, morfamquat,morfamquat dichloride, moroxydine, moroxydine hydrochloride,morphothion, morzid, moxidectin, MSMA, muscalure, myclobutanil,myclozolin, N-(ethylmercury)-p-toluenesulphonanilide, nabam, naftalofos,naled, naphthalene, naphthaleneacetamide, naphthalic anhydride,naphthoxyacetic acids, naproanilide, napropamide, napropamide-M,naptalam, naptalam-sodium, natamycin, neburon, niclosamide,niclosamide-olamine, nicosulfuron, nicotine, nifluridide, nipyraclofen,nitenpyram, nithiazine, nitralin, nitrapyrin, nitrilacarb, nitrofen,nitrofluorfen, nitrostyrene, nitrothal-isopropyl, norbormide,norflurazon, nornicotine, noruron, novaluron, noviflumuron, nuarimol,OCH, octachlorodipropyl ether, octhilinone, ofurace, omethoate,orbencarb, orfralure, ortho-dichlorobenzene, orthosulfamuron,oryctalure, orysastrobin, oryzalin, osthol, ostramone, oxabetrinil,oxadiargyl, oxadiazon, oxadixyl, oxamate, oxamyl, oxapyrazon,oxapyrazon-dimolamine, oxapyrazon-sodium, oxasulfuron, oxathiapiprolin,oxaziclomefone, oxine-copper, oxolinic acid, oxpoconazole, oxpoconazolefumarate, oxycarboxin, oxydemeton-methyl, oxydeprofos, oxydisulfoton,oxyfluorfen, oxymatrine, oxytetracycline, oxytetracycline hydrochloride,paclobutrazol, paichongding, para-dichlorobenzene, parafluron, paraquat,paraquat dichloride, paraquat dimetilsulfate, parathion,parathion-methyl, parinol, pebulate, pefurazoate, pelargonic acid,penconazole, pencycuron, pendimethalin, penflufen, penfluron,penoxsulam, pentachlorophenol, pentachlorophenyl laurate, pentanochlor,penthiopyrad, pentmethrin, pentoxazone, perfluidone, permethrin,pethoxamid, phenamacril, phenazine oxide, phenisopham, phenkapton,phenmedipham, phenmedipham-ethyl, phenobenzuron, phenothrin,phenproxide, phenthoate, phenylmercuriurea, phenylmercury acetate,phenylmercury chloride, phenylmercury derivative of pyrocatechol,phenylmercury nitrate, phenylmercury salicylate, phorate, phosacetim,phosalone, phosdiphen, phosfolan, phosfolan-methyl, phosglycin, phosmet,phosnichlor, phosphamidon, phosphine, phosphocarb, phosphorus, phostin,phoxim, phoxim-methyl, phthalide, picarbutrazox, picloram,picloram-2-ethylhexyl, picloram-isoctyl, picloram-methyl,picloram-olamine, picloram-potassium, picloram-triethylammonium,picloram-tris(2-hydroxypropyl)ammonium, picolinafen, picoxystrobin,pindone, pindone-sodium, pinoxaden, piperalin, piperonyl butoxide,piperonyl cyclonene, piperophos, piproctanyl, piproctanyl bromide,piprotal, pirimetaphos, pirimicarb, pirimioxyphos, pirimiphos-ethyl,pirimiphos-methyl, plifenate, polycarbamate, polyoxins, polyoxorim,polyoxorim-zinc, polythialan, potassium arsenite, potassium azide,potassium cyanate, potassium gibberellate, potassium naphthenate,potassium polysulfide, potassium thiocyanate, potassiumα-naphthaleneacetate, pp′-DDT, prallethrin, precocene I, precocene II,precocene III, pretilachlor, primidophos, primisulfuron,primisulfuron-methyl, probenazole, prochloraz, prochloraz-manganese,proclonol, procyazine, procymidone, prodiamine, profenofos, profluazol,profluralin, profluthrin, profoxydim, proglinazine, proglinazine-ethyl,prohexadione, prohexadione-calcium, prohydrojasmon, promacyl, promecarb,prometon, prometryn, promurit, propachlor, propamidine, propamidinedihydrochloride, propamocarb, propamocarb hydrochloride, propanil,propaphos, propaquizafop, propargite, proparthrin, propazine,propetamphos, propham, propiconazole, propineb, propisochlor, propoxur,propoxycarbazone, propoxycarbazone-sodium, propyl isome,propyrisulfuron, propyzamide, proquinazid, prosuler, prosulfalin,prosulfocarb, prosulfuron, prothidathion, prothiocarb, prothiocarbhydrochloride, prothioconazole, prothiofos, prothoate, protrifenbute,proxan, proxan-sodium, prynachlor, pydanon, pyflubumide, pymetrozine,pyracarbolid, pyraclofos, pyraclonil, pyraclostrobin, pyraflufen,pyraflufen-ethyl, pyrafluprole, pyramat, pyrametostrobin,pyraoxystrobin, pyrasulfotole, pyrazolynate, pyrazophos, pyrazosulfuron,pyrazosulfuron-ethyl, pyrazothion, pyrazoxyfen, pyresmethrin, pyrethrinI, pyrethrin II, pyrethrins, pyribambenz-isopropyl, pyribambenz-propyl,pyribencarb, pyribenzoxim, pyributicarb, pyriclor, pyridaben, pyridafol,pyridalyl, pyridaphenthion, pyridate, pyridinitril, pyrifenox,pyrifluquinazon, pyriftalid, pyrimethanil, pyrimidifen, pyriminobac,pyriminobac-methyl, pyriminostrobin, pyrimisulfan, pyrimitate,pyrinuron, pyriofenone, pyriprole, pyripropanol, pyriproxyfen,pyrisoxazole, pyrithiobac, pyrithiobac-sodium, pyrolan, pyroquilon,pyroxasulfone, pyroxsulam, pyroxychlor, pyroxyfur, quassia, quinacetol,quinacetol sulfate, quinalphos, quinalphos-methyl, quinazamid,quinclorac, quinconazole, quinmerac, quinoclamine, quinonamid,quinothion, quinoxyfen, quintiofos, quintozene, quizalofop,quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl,quizalofop-P-tefuryl, quwenzhi, quyingding, rabenzazole, rafoxanide,rebemide, rescalure, resmethrin, rhodethanil, rhodojaponin-III,ribavirin, rimsulfuron, rotenone, ryania, saflufenacil, saijunmao,saisentong, salicylanilide, sanguinarine, santonin, schradan,scilliroside, sebuthylazine, secbumeton, sedaxane, selamectin,semiamitraz, semiamitraz chloride, sesamex, sesamolin, sethoxydim,shuangjiaancaolin, siduron, siglure, silafluofen, silatrane, silica gel,silthiofam, simazine, simeconazole, simeton, simetryn, sintofen, SMA,S-metolachlor, sodium arsenite, sodium azide, sodium chlorate, sodiumfluoride, sodium fluoroacetate, sodium hexafluorosilicate, sodiumnaphthenate, sodium orthophenylphenoxide, sodium pentachlorophenoxide,sodium polysulfide, sodium thiocyanate, sodium α-naphthaleneacetate,sophamide, spinetoram, spinosad, spirodiclofen, spiromesifen,spirotetramat, spiroxamine, streptomycin, streptomycin sesquisulfate,strychnine, sulcatol, sulcofuron, sulcofuron-sodium, sulcotrione,sulfallate, sulfentrazone, sulfiram, sulfluramid, sulfometuron,sulfometuron-methyl, sulfosulfuron, sulfotep, sulfoxaflor, sulfoxide,sulfoxime, sulfur, sulfuric acid, sulfuryl fluoride, sulglycapin,sulprofos, sultropen, swep, tau-fluvalinate, tavron, tazimcarb, TCA,TCA-ammonium, TCA-calcium, TCA-ethadyl, TCA-magnesium, TCA-sodium, TDE,tebuconazole, tebufenozide, tebufenpyrad, tebufloquin, tebupirimfos,tebutam, tebuthiuron, tecloftalam, tecnazene, tecoram, teflubenzuron,tefluthrin, tefuryltrione, tembotrione, temephos, tepa, TEPP,tepraloxydim, terallethrin, terbacil, terbucarb, terbuchlor, terbufos,terbumeton, terbuthylazine, terbutryn, tetcyclacis, tetrachloroethane,tetrachlorvinphos, tetraconazole, tetradifon, tetrafluron, tetramethrin,tetramethylfluthrin, tetramine, tetranactin, tetraniliprole, tetrasul,thallium sulfate, thenylchlor, theta-cypermethrin, thiabendazole,thiacloprid, thiadifluor, thiamethoxam, thiapronil, thiazafluron,thiazopyr, thicrofos, thicyofen, thidiazimin, thidiazuron,thiencarbazone, thiencarbazone-methyl, thifensulfuron,thifensulfuron-methyl, thifluzamide, thiobencarb, thiocarboxime,thiochlorfenphim, thiocyclam, thiocyclam hydrochloride, thiocyclamoxalate, thiodiazole-copper, thiodicarb, thiofanox, thiofluoximate,thiohempa, thiomersal, thiometon, thionazin, thiophanate,thiophanate-methyl, thioquinox, thiosemicarbazide, thiosultap,thiosultap-diammonium, thiosultap-disodium, thiosultap-monosodium,thiotepa, thiram, thuringiensin, tiadinil, tiafenacil, tiaojiean,tiocarbazil, tioclorim, tioxazafen, tioxymid, tirpate, tolclofos-methyl,tolfenpyrad, tolprocarb, tolpyralate, tolylfluanid, tolylmercuryacetate, topramezone, tralkoxydim, tralocythrin, tralomethrin,tralopyril, transfluthrin, transpermethrin, tretamine, triacontanol,triadimefon, triadimenol, triafamone, tri-allate, triamiphos,triapenthenol, triarathene, triarimol, triasulfuron, triazamate,triazbutil, triaziflam, triazophos, triazoxide, tribenuron,tribenuron-methyl, tribufos, tributyltin oxide, tricamba, trichlamide,trichlorfon, trichlormetaphos-3, trichloronat, triclopyr,triclopyr-butotyl, triclopyr-ethyl, triclopyricarb,triclopyr-triethylammonium, tricyclazole, tridemorph, tridiphane,trietazine, trifenmorph, trifenofos, trifloxystrobin, trifloxysulfuron,trifloxysulfuron-sodium, trifludimoxazin, triflumezopyrim, triflumizole,triflumuron, trifluralin, triflusulfuron, triflusulfuron-methyl, trifop,trifop-methyl, trifopsime, triforine, trihydroxytriazine, trimedlure,trimethacarb, trimeturon, trinexapac, trinexapac-ethyl, triprene,tripropindan, triptolide, tritac, triticonazole, tritosulfuron,trunc-call, uniconazole, uniconazole-P, urbacide, uredepa, valerate,validamycin, valifenalate, valone, vamidothion, vangard, vaniliprole,vernolate, vinclozolin, warfarin, warfarin-potassium, warfarin-sodium,xiaochongliulin, xinjunan, xiwojunan, XMC, xylachlor, xylenols,xylylcarb, yishijing, zarilamid, zeatin, zengxiaoan, zeta-cypermethrin,zinc naphthenate, zinc phosphide, zinc thiazole, zineb, ziram,zolaprofos, zoxamide, zuomihuanglong, α-chlorohydrin, α-ecdysone,α-multistriatin, and α-naphthaleneacetic acid. For more informationconsult the “COMPENDIUM OF PESTICIDE COMMON NAMES” located atalanwood.net. Also consult “THE PESTICIDE MANUAL” 15th Edition, editedby C D S Tomlin, copyright 2009 by British Crop Production Council, orits prior, or more recent editions.

In another embodiment, molecules of Formula One may also be used incombination (such as in a compositional mixture, or a simultaneous orsequential application) with the following compound.

In another embodiment, molecules of Formula One may also be used incombination (such as in a compositional mixture, or a simultaneous orsequential application) with one or more biopesticides. The term“biopesticide” is used for microbial biological pest control agents thatare applied in a similar manner to chemical pesticides. Commonly theseare bacterial, but there are also examples of fungal control agents,including Trichoderma spp. and Ampelomyces quisqualis (a control agentfor grape powdery mildew). Bacillus subtilis are used to control plantpathogens. Weeds and rodents have also been controlled with microbialagents. One well-known insecticide example is Bacillus thuringiensis, abacterial disease of Lepidoptera, Coleoptera, and Diptera. Because ithas little effect on other organisms, it is considered moreenvironmentally friendly than synthetic pesticides. Biologicalinsecticides include products based on: entomopathogenic fungi (e.g.Metarhizium anisopliae); entomopathogenic nematodes (e.g. Steinernemafeltiae); and entomopathogenic viruses (e.g. Cydia pomonellagranulovirus).

Other examples of entomopathogenic organisms include, but are notlimited to, baculoviruses, bacteria and other prokaryotic organisms,fungi, protozoa and Microsproridia. Biologically derived insecticidesinclude, but not limited to, rotenone, veratridine, as well as microbialtoxins; insect tolerant or resistant plant varieties; and organismsmodified by recombinant DNA technology to either produce insecticides orto convey an insect resistant property to the genetically modifiedorganism. In one embodiment, the molecules of Formula One may be usedwith one or more biopesticides in the area of seed treatments and soilamendments. The Manual of Biocontrol Agents gives a review of theavailable biological insecticide (and other biology-based control)products. Copping L. G. (ed.) (2004). The Manual of Biocontrol Agents(formerly the Biopesticide Manual) 3rd Edition. British Crop ProductionCouncil (BCPC), Farnham, Surrey UK.

In another embodiment, the above possible combinations may be used in awide variety of weight ratios. For example, a two component mixture, theweight ratio of a molecule of Formula One to another compound, can befrom about 100:1 to about 1:100; in another example the weight ratio canbe about 50:1 to about 1:50; in another example the weight ratio can beabout 20:1 to about 1 to 20; in another example the weight ratio can beabout 10:1 to about 1:10; in another example the weight ratio can beabout 5:1 to 1:5; in another example the weight ratio can be about 3:1to about 1:3; in another example the weight ratio can be about 2:1 toabout 1:2; and in a final example the weight ratio can be about 1:1.However, preferably, weight ratios less than about 10:1 to about 1:10are preferred. It is also preferred sometimes to use a three or fourcomponent mixture comprising one or more molecules of Formula One andone or more other compounds from the above possible combinations.

TABLE A Range of the Weight Ratio of a molecule No. of the Formula Oneto another compound 1 100:1 to 1:100 2 50:1 to 1:50 3 20:1 to 1:20 410:1 to 1:10 5 5:1 to 1:5 6 3:1 to 1:3 7 2:1 to 1:2 8 1:1Weight ratios of a molecule of the Formula One or any agriculturallyacceptable salt thereof to another compound envisioned to be synergisticpesticidal compositions may be depicted as X:Y; wherein X is the partsby weight of a molecule of the Formula One or any agriculturallyacceptable salt thereof, and Y is the parts by weight of anothercompound. The numerical range of the parts by weight for X is 0<X≦100and the parts by weight for Y is 0<Y≦100 as shown graphically in TABLEB. By way of non-limiting example, the weight ratio of the pesticide toanother compound may be about 20:1.

TABLE B Another 100 X, Y X, Y Compound 50 X, Y X, Y X, Y (Y) Parts 20 X,Y X, Y X, Y X, Y by weight 15 X, Y X, Y X, Y 10 X, Y X, Y 5 X, Y X, Y X,Y X, Y 3 X, Y X, Y X, Y X, Y X, Y X, Y X, Y 2 X, Y X, Y X, Y X, Y X, Y 1X, Y X, Y X, Y X, Y X, Y X, Y X, Y X, Y X, Y 1 2 3 5 10 15 20 50 100Molecule of the Formula One (X) Parts by weight

Ranges of weight ratios of a molecule of the Formula One or anyagriculturally acceptable salt thereof to another compound envisioned tobe synergistic pesticidal compositions may be depicted as X₁:Y₁ toX₂:Y₂, wherein X and Y are defined as above. In one particularembodiment, the range of weight ratios may be X₁:Y₁ to X₂:Y₂, whereinX₁>Y₁ and X₂<Y₂. By way of non-limiting example, the range of weightratios of a molecule of the Formula One or any agriculturally acceptablesalt thereof to another compound may be between about 3:1 and about 1:3.In some embodiments, the range of weight ratios may be X₁:Y₁ to X₂:Y₂,wherein X₁>Y₁ and X₂>Y₂. By way of non-limiting example, the range of amolecule of the Formula One or any agriculturally acceptable saltthereof to another compound may be between about 15:1 and about 3:1. Infurther embodiments, the range of weight ratios may be X₁:Y₁ to X₂:Y₂,wherein X₁<Y₁ and X₂<Y₂. By way of non-limiting example, the range ofweight ratios of a molecule of the Formula One or any agriculturallyacceptable salt thereof to another compound may be between about 1:3 andabout 1:20.

Formulations

A pesticide is rarely suitable for application in its pure form. It isusually necessary to add other substances so that the pesticide can beused at the required concentration and in an appropriate form,permitting ease of application, handling, transportation, storage, andmaximum pesticide activity. Thus, pesticides are formulated into, forexample, baits, concentrated emulsions, dusts, emulsifiableconcentrates, fumigants, gels, granules, microencapsulations, seedtreatments, suspension concentrates, suspoemulsions, tablets, watersoluble liquids, water dispersible granules or dry flowables, wettablepowders, and ultra-low volume solutions. For further information onformulation types see “Catalogue of Pesticide Formulation Types andInternational Coding System” Technical Monograph n° 2, 5th Edition byCropLife International (2002).

Pesticides are applied most often as aqueous suspensions or emulsionsprepared from concentrated formulations of such pesticides. Suchwater-soluble, water-suspendable, or emulsifiable formulations areeither solids, usually known as wettable powders, or water dispersiblegranules, or liquids usually known as emulsifiable concentrates, oraqueous suspensions. Wettable powders, which may be compacted to formwater dispersible granules, comprise an intimate mixture of thepesticide, a carrier, and surfactants. The concentration of thepesticide is usually from about 10% to about 90% by weight. The carrieris usually selected from among the attapulgite clays, themontmorillonite clays, the diatomaceous earths, or the purifiedsilicates. Effective surfactants, comprising from about 0.5% to about10% of the wettable powder, are found among sulfonated lignins,condensed naphthalenesulfonates, naphthalenesulfonates,alkylbenzenesulfonates, alkyl sulfates, and non-ionic surfactants suchas ethylene oxide adducts of alkyl phenols.

Emulsifiable concentrates of pesticides comprise a convenientconcentration of a pesticide, such as from about 50 to about 500 gramsper liter of liquid dissolved in a carrier that is either a watermiscible solvent or a mixture of water-immiscible organic solvent andemulsifiers. Useful organic solvents include aromatics, especiallyxylenes and petroleum fractions, especially the high-boilingnaphthalenic and olefinic portions of petroleum such as heavy aromaticnaphtha. Other organic solvents may also be used, such as the terpenicsolvents including rosin derivatives, aliphatic ketones such ascyclohexanone, and complex alcohols such as 2-ethoxyethanol. Suitableemulsifiers for emulsifiable concentrates are selected from conventionalanionic and non-ionic surfactants.

Aqueous suspensions comprise suspensions of water-insoluble pesticidesdispersed in an aqueous carrier at a concentration in the range fromabout 5% to about 50% by weight. Suspensions are prepared by finelygrinding the pesticide and vigorously mixing it into a carrier comprisedof water and surfactants. Ingredients, such as inorganic salts andsynthetic or natural gums may also be added, to increase the density andviscosity of the aqueous carrier. It is often most effective to grindand mix the pesticide at the same time by preparing the aqueous mixtureand homogenizing it in an implement such as a sand mill, ball mill, orpiston-type homogenizer.

Pesticides may also be applied as granular compositions that areparticularly useful for applications to the soil. Granular compositionsusually contain from about 0.5% to about 10% by weight of the pesticide,dispersed in a carrier that comprises clay or a similar substance. Suchcompositions are usually prepared by dissolving the pesticide in asuitable solvent and applying it to a granular carrier which has beenpre-formed to the appropriate particle size, in the range of from about0.5 to about 3 mm. Such compositions may also be formulated by making adough or paste of the carrier and compound and crushing and drying toobtain the desired granular particle size.

Dusts containing a pesticide are prepared by intimately mixing thepesticide in powdered form with a suitable dusty agricultural carrier,such as kaolin clay, ground volcanic rock, and the like. Dusts cansuitably contain from about 1% to about 10% of the pesticide. They canbe applied as a seed dressing or as a foliage application with a dustblower machine.

It is equally practical to apply a pesticide in the form of a solutionin an appropriate organic solvent, usually petroleum oil, such as thespray oils, which are widely used in agricultural chemistry.

Pesticides can also be applied in the form of an aerosol composition. Insuch compositions the pesticide is dissolved or dispersed in a carrier,which is a pressure-generating propellant mixture. The aerosolcomposition is packaged in a container from which the mixture isdispensed through an atomizing valve.

Pesticide baits are formed when the pesticide is mixed with food or anattractant or both. When the pests eat the bait they also consume thepesticide. Baits may take the form of granules, gels, flowable powders,liquids, or solids. They can be used in pest harborages.

Fumigants are pesticides that have a relatively high vapor pressure andhence can exist as a gas in sufficient concentrations to kill pests insoil or enclosed spaces. The toxicity of the fumigant is proportional toits concentration and the exposure time. They are characterized by agood capacity for diffusion and act by penetrating the pest'srespiratory system or being absorbed through the pest's cuticle.Fumigants are applied to control stored product pests under gas proofsheets, in gas sealed rooms or buildings or in special chambers.

Pesticides can be microencapsulated by suspending the pesticideparticles or droplets in plastic polymers of various types. By alteringthe chemistry of the polymer or by changing factors in the processing,microcapsules can be formed of various sizes, solubility, wallthicknesses, and degrees of penetrability. These factors govern thespeed with which the active ingredient within is released, which inturn, affects the residual performance, speed of action, and odor of theproduct.

Oil solution concentrates are made by dissolving pesticide in a solventthat will hold the pesticide in solution. Oil solutions of a pesticideusually provide faster knockdown and kill of pests than otherformulations due to the solvents themselves having pesticidal action andthe dissolution of the waxy covering of the integument increasing thespeed of uptake of the pesticide. Other advantages of oil solutionsinclude better storage stability, better penetration of crevices, andbetter adhesion to greasy surfaces.

Another embodiment is an oil-in-water emulsion, wherein the emulsioncomprises oily globules which are each provided with a lamellar liquidcrystal coating and are dispersed in an aqueous phase, wherein each oilyglobule comprises at least one compound which is agriculturally active,and is individually coated with a monolamellar or oligolamellar layercomprising: (1) at least one non-ionic lipophilic surface-active agent,(2) at least one non-ionic hydrophilic surface-active agent and (3) atleast one ionic surface-active agent, wherein the globules having a meanparticle diameter of less than 800 nanometers. Further information onthe embodiment is disclosed in U.S. patent publication 20070027034published Feb. 1, 2007, having patent application Ser. No. 11/495,228.For ease of use, this embodiment will be referred to as “OIWE”.

For further information consult “Insect Pest Management” 2nd Edition byD. Dent, copyright CAB International (2000). Additionally, for moredetailed information consult “Handbook of Pest Control—The Behavior,Life History, and Control of Household Pests” by Arnold Mallis, 9thEdition, copyright 2004 by GIE Media Inc.

Other Formulation Components

Generally, when the molecules disclosed in Formula One are used in aformulation, such formulation can also contain other components. Thesecomponents include, but are not limited to, (this is a non-exhaustiveand non-mutually exclusive list) wetters, spreaders, stickers,penetrants, buffers, sequestering agents, drift reduction agents,compatibility agents, anti-foam agents, cleaning agents, andemulsifiers. A few components are described forthwith.

A wetting agent is a substance that when added to a liquid increases thespreading or penetration power of the liquid by reducing the interfacialtension between the liquid and the surface on which it is spreading.Wetting agents are used for two main functions in agrochemicalformulations: during processing and manufacture to increase the rate ofwetting of powders in water to make concentrates for soluble liquids orsuspension concentrates; and during mixing of a product with water in aspray tank to reduce the wetting time of wettable powders and to improvethe penetration of water into water-dispersible granules. Examples ofwetting agents used in wettable powder, suspension concentrate, andwater-dispersible granule formulations are: sodium lauryl sulfate;sodium dioctyl sulfosuccinate; alkyl phenol ethoxylates; and aliphaticalcohol ethoxylates.

A dispersing agent is a substance which adsorbs onto the surface ofparticles and helps to preserve the state of dispersion of the particlesand prevents them from reaggregating. Dispersing agents are added toagrochemical formulations to facilitate dispersion and suspension duringmanufacture, and to ensure the particles redisperse into water in aspray tank. They are widely used in wettable powders, suspensionconcentrates and water-dispersible granules. Surfactants that are usedas dispersing agents have the ability to adsorb strongly onto a particlesurface and provide a charged or steric barrier to reaggregation ofparticles. The most commonly used surfactants are anionic, non-ionic, ormixtures of the two types. For wettable powder formulations, the mostcommon dispersing agents are sodium lignosulfonates. For suspensionconcentrates, very good adsorption and stabilization are obtained usingpolyelectrolytes, such as sodium naphthalene sulfonate formaldehydecondensates. Tristyrylphenol ethoxylate phosphate esters are also used.Non-ionics such as alkylarylethylene oxide condensates and EO-PO blockcopolymers are sometimes combined with anionics as dispersing agents forsuspension concentrates. In recent years, new types of very highmolecular weight polymeric surfactants have been developed as dispersingagents. These have very long hydrophobic ‘backbones’ and a large numberof ethylene oxide chains forming the ‘teeth’ of a ‘comb’ surfactant.These high molecular weight polymers can give very good long-termstability to suspension concentrates because the hydrophobic backboneshave many anchoring points onto the particle surfaces. Examples ofdispersing agents used in agrochemical formulations are: sodiumlignosulfonates; sodium naphthalene sulfonate formaldehyde condensates;tristyrylphenol ethoxylate phosphate esters; aliphatic alcoholethoxylates; alkyl ethoxylates; EO-PO block copolymers; and graftcopolymers.

An emulsifying agent is a substance which stabilizes a suspension ofdroplets of one liquid phase in another liquid phase. Without theemulsifying agent the two liquids would separate into two immiscibleliquid phases. The most commonly used emulsifier blends containalkylphenol or aliphatic alcohol with twelve or more ethylene oxideunits and the oil-soluble calcium salt of dodecylbenzenesulfonic acid. Arange of hydrophile-lipophile balance (“HLB”) values from 8 to 18 willnormally provide good stable emulsions. Emulsion stability can sometimesbe improved by the addition of a small amount of an EO-PO blockcopolymer surfactant.

A solubilizing agent is a surfactant which will form micelles in waterat concentrations above the critical micelle concentration. The micellesare then able to dissolve or solubilize water-insoluble materials insidethe hydrophobic part of the micelle. The types of surfactants usuallyused for solubilization are non-ionics, sorbitan monooleates, sorbitanmonooleate ethoxylates, and methyl oleate esters.

Surfactants are sometimes used, either alone or with other additivessuch as mineral or vegetable oils as adjuvants to spray-tank mixes toimprove the biological performance of the pesticide on the target. Thetypes of surfactants used for bioenhancement depend generally on thenature and mode of action of the pesticide. However, they are oftennon-ionics such as: alkyl ethoxylates; linear aliphatic alcoholethoxylates; aliphatic amine ethoxylates.

A carrier or diluent in an agricultural formulation is a material addedto the pesticide to give a product of the required strength. Carriersare usually materials with high absorptive capacities, while diluentsare usually materials with low absorptive capacities. Carriers anddiluents are used in the formulation of dusts, wettable powders,granules and water-dispersible granules.

Organic solvents are used mainly in the formulation of emulsifiableconcentrates, oil-in-water emulsions, suspoemulsions, and ultra-lowvolume formulations, and to a lesser extent, granular formulations.Sometimes mixtures of solvents are used. The first main groups ofsolvents are aliphatic paraffinic oils such as kerosene or refinedparaffins. The second main group (and the most common) comprises thearomatic solvents such as xylene and higher molecular weight fractionsof C9 and C10 aromatic solvents. Chlorinated hydrocarbons are useful ascosolvents to prevent crystallization of pesticides when the formulationis emulsified into water. Alcohols are sometimes used as cosolvents toincrease solvent power. Other solvents may include vegetable oils, seedoils, and esters of vegetable and seed oils.

Thickeners or gelling agents are used mainly in the formulation ofsuspension concentrates, emulsions and suspoemulsions to modify therheology or flow properties of the liquid and to prevent separation andsettling of the dispersed particles or droplets. Thickening, gelling,and anti-settling agents generally fall into two categories, namelywater-insoluble particulates and water-soluble polymers. It is possibleto produce suspension concentrate formulations using clays and silicas.Examples of these types of materials, include, but are not limited to,montmorillonite, bentonite, magnesium aluminum silicate, andattapulgite. Water-soluble polysaccharides have been used asthickening-gelling agents for many years. The types of polysaccharidesmost commonly used are natural extracts of seeds and seaweeds or aresynthetic derivatives of cellulose. Examples of these types of materialsinclude, but are not limited to, guar gum; locust bean gum; carrageenam;alginates; methyl cellulose; sodium carboxymethyl cellulose (SCMC);hydroxyethyl cellulose (HEC). Other types of anti-settling agents arebased on modified starches, polyacrylates, polyvinyl alcohol andpolyethylene oxide. Another good anti-settling agent is xanthan gum.

Microorganisms can cause spoilage of formulated products. Thereforepreservation agents are used to eliminate or reduce their effect.Examples of such agents include, but are not limited to: propionic acidand its sodium salt; sorbic acid and its sodium or potassium salts;benzoic acid and its sodium salt; p-hydroxybenzoic acid sodium salt;methyl p-hydroxybenzoate; and 1,2-benzisothiazolin-3-one (BIT).

The presence of surfactants often causes water-based formulations tofoam during mixing operations in production and in application through aspray tank. In order to reduce the tendency to foam, anti-foam agentsare often added either during the production stage or before fillinginto bottles. Generally, there are two types of anti-foam agents, namelysilicones and non-silicones. Silicones are usually aqueous emulsions ofdimethyl polysiloxane, while the non-silicone anti-foam agents arewater-insoluble oils, such as octanol and nonanol, or silica. In bothcases, the function of the anti-foam agent is to displace the surfactantfrom the air-water interface.

“Green” agents (e.g., adjuvants, surfactants, solvents) can reduce theoverall environmental footprint of crop protection formulations. Greenagents are biodegradable and generally derived from natural and/orsustainable sources, e.g. plant and animal sources. Specific examplesare: vegetable oils, seed oils, and esters thereof, also alkoxylatedalkyl polyglucosides.

For further information, see “Chemistry and Technology of AgrochemicalFormulations” edited by D. A. Knowles, copyright 1998 by Kluwer AcademicPublishers. Also see “Insecticides in Agriculture andEnvironment—Retrospects and Prospects” by A. S. Perry, I. Yamamoto, I.Ishaaya, and R. Perry, copyright 1998 by Springer-Verlag.

Pests

In general, the molecules of Formula One may be used to control pestse.g. ants, aphids, beetles, bristletails, cockroaches, crickets,earwigs, fleas, flies, grasshoppers, leafhoppers, lice, locusts, mites,moths, nematodes, scales, symphylans, termites, thrips, ticks, wasps,and whiteflies.

In another embodiment, the molecules of Formula One may be used tocontrol pests in the Phyla Nematoda and/or Arthropoda.

In another embodiment, the molecules of Formula One may be used tocontrol pests in the Subphyla Chelicerata, Myriapoda, and/or Hexapoda.

In another embodiment, the molecules of Formula One may be used tocontrol pests in the Classes of Arachnida, Symphyla, and/or Insecta.

In another embodiment, the molecules of Formula One may be used tocontrol pests of the Order Anoplura. A non-exhaustive list of particulargenera includes, but is not limited to, Haematopinus spp., Hoplopleuraspp., Linognathus spp., Pediculus spp., and Polyplax spp. Anon-exhaustive list of particular species includes, but is not limitedto, Haematopinus asini, Haematopinus suis, Linognathus setosus,Linognathus ovillus, Pediculus humanus capitis, Pediculus humanushumanus, and Pthirus pubis.

In another embodiment, the molecules of Formula One may be used tocontrol pests in the Order Coleoptera. A non-exhaustive list ofparticular genera includes, but is not limited to, Acanthoscelides spp.,Agriotes spp., Anthonomus spp., Apion spp., Apogonia spp., Aulacophoraspp., Bruchus spp., Cerosterna spp., Cerotoma spp., Ceutorhynchus spp.,Chaetocnema spp., Colaspis spp., Ctenicera spp., Curculio spp.,Cyclocephala spp., Diabrotica spp., Hypera spp., Ips spp., Lyctus spp.,Megascelis spp., Meligethes spp., Otiorhynchus spp., Pantomorus spp.,Phyllophaga spp., Phyllotreta spp., Rhizotrogus spp., Rhynchites spp.,Rhynchophorus spp., Scolytus spp., Sphenophorus spp., Sitophilus spp.,and Tribolium spp. A non-exhaustive list of particular species includes,but is not limited to, Acanthoscelides obtectus, Agrilus planipennis,Anoplophora glabripennis, Anthonomus grandis, Ataenius spretulus,Atomaria linearis, Bothynoderes punctiventris, Bruchus pisorum,Callosobruchus maculatus, Carpophilus hemipterus, Cassida vittata,Cerotoma trifurcata, Ceutorhynchus assimilis, Ceutorhynchus napi,Conoderus scalaris, Conoderus stigmosus, Conotrachelus nenuphar, Cotinisnitida, Crioceris asparagi, Cryptolestes ferrugineus, Cryptolestespusillus, Cryptolestes turcicus, Cylindrocopturus adspersus, Deporausmarginatus, Dermestes lardarius, Dermestes maculatus, Epilachnavarivestis, Faustinus cubae, Hylobius pales, Hypera postica,Hypothenemus hampei, Lasioderma serricome, Leptinotarsa decemlineata,Liogenys fuscus, Liogenys suturalis, Lissorhoptrus oryzophilus,Maecolaspis joliveti, Melanotus communis, Meligethes aeneus, Melolonthamelolontha, Oberea brevis, Oberea linearis, Oryctes rhinoceros,Oryzaephilus mercator, Oryzaephilus surinamensis, Oulema melanopus,Oulema oryzae, Phyllophaga cuyabana, Popillia japonica, Prostephanustruncatus, Rhyzopertha dominica, Sitona lineatus, Sitophilus granarius,Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum, Triboliumcastaneum, Tribolium confusum, Trogoderma variabile, and Zabrustenebrioides.

In another embodiment, the molecules of Formula One may be used tocontrol pests of the Order Dermaptera.

In another embodiment, the molecules of Formula One may be used tocontrol pests of the Order Blattaria. A non-exhaustive list ofparticular species includes, but is not limited to, Blattella germanica,Blatta orientalis, Parcoblatta pennsylvanica, Periplaneta americana,Periplaneta australasiae, Periplaneta brunnea, Periplaneta fuliginosa,Pycnoscelus surinamensis, and Supella longipalpa.

In another embodiment, the molecules of Formula One may be used tocontrol pests of the Order Diptera. A non-exhaustive list of particulargenera includes, but is not limited to, Aedes spp., Agromyza spp.,Anastrepha spp., Anopheles spp., Bactrocera spp., Ceratitis spp.,Chrysops spp., Cochliomyia spp., Contarinia spp., Culex spp., Dasineuraspp., Delia spp., Drosophila spp., Fannia spp., Hylemyia spp., Liriomyzaspp., Musca spp., Phorbia spp., Tabanus spp., and Tipula spp. Anon-exhaustive list of particular species includes, but is not limitedto, Agromyza frontella, Anastrepha suspensa, Anastrepha ludens,Anastrepha obliqa, Bactrocera cucurbitae, Bactrocera dorsalis,Bactrocera invadens, Bactrocera zonata, Ceratitis capitata, Dasineurabrassicae, Delia platura, Fannia canicularis, Fannia scalaris,Gasterophilus intestinalis, Gracillia perseae, Haematobia irritans,Hypoderma lineatum, Liriomyza brassicae, Melophagus ovinus, Muscaautumnalis, Musca domestics, Oestrus ovis, Oscinella frit, Pegomyabetae, Psila rosae, Rhagoletis cerasi, Rhagoletis pomonella, Rhagoletismendax, Sitodiplosis mosellana, and Stomoxys calcitrans.

In another embodiment, the molecules of Formula One may be used tocontrol pests of the Order Hemiptera. A non-exhaustive list ofparticular genera includes, but is not limited to, Adelges spp.,Aulacaspis spp., Aphrophora spp., Aphis spp., Bemisia spp., Ceroplastesspp., Chionaspis spp., Chlysomphalus spp., Coccus spp., Empoasca spp.,Lepidosaphes spp., Lagynotomus spp., Lygus spp., Macrosiphum spp.,Nephotettix spp., Nezara spp., Philaenus spp., Phytocoris spp.,Piezodorus spp., Planococcus spp., Pseudococcus spp., Rhopalosiphumspp., Saissetia spp., Therioaphis spp., Toumeyella spp., Toxoptera spp.,Trialeurodes spp., Triatoma spp. and Unaspis spp. A non-exhaustive listof particular species includes, but is not limited to, Acrosternumhilare, Acyrthosiphon pisum, Aleyrodes proletella, Aleurodicusdispersus, Aleurothrixus floccosus, Amrasca biguttula biguttula,Aonidiella aurantii, Aphis gossypii, Aphis glycines, Aphis pomi,Aulacorthum solani, Bemisia argentifolii, Bemisia tabaci, Blissusleucopterus, Brachycorynella asparagi, Brevennia rehi, Brevicorynebrassicae, Calocoris norvegicus, Ceroplastes rubens, Cimex hemipterus,Cimex lectularius, Dagbertus fasciatus, Dichelops furcatus, Diuraphisnoxia, Diaphorina citri, Dysaphis plantaginea, Dysdercus suturellus,Edessa meditabunda, Eriosoma lanigerum, Eurygaster maura, Euschistusheros, Euschistus servus, Helopeltis antonii, Helopeltis theivora,Icerya purchasi, Idioscopus nitidulus, Laodelphax striatellus,Leptocorisa oratorius, Leptocorisa varicornis, Lygus hesperus,Maconellicoccus hirsutus, Macrosiphum euphorbiae, Macrosiphum granarium,Macrosiphum rosae, Macrosteles quadrilineatus, Mahanarva frimbiolata,Metopolophium dirhodum, Mictis longicornis, Myzus persicae, Nephotettixcinctipes, Neurocolpus longirostris, Nezara viridula, Nilaparvatalugens, Parlatoria pergandii, Parlatoria ziziphi, Peregrinus maidis,Phylloxera vitifoliae, Physokermes piceae, Phytocoris californicus,Phytocoris relativus, Piezodorus guildinii, Poecilocapsus lineatus,Psallus vaccinicola, Pseudacysta perseae, Pseudococcus brevipes,Quadraspidiotus perniciosus, Rhopalosiphum maidis, Rhopalosiphum padi,Saissetia oleae, Scaptocoris castanea, Schizaphis graminum, Sitobionavenae, Sogatella furcifera, Trialeurodes vaporariorum, Trialeurodesabutiloneus, Unaspis yanonensis, and Zulia entrerriana.

In another embodiment, the molecules of Formula One may be used tocontrol pests of the Order Hymenoptera. A non-exhaustive list ofparticular genera includes, but is not limited to, Acromyrmex spp., Attaspp., Camponotus spp., Diprion spp., Formica spp., Monomorium spp.,Neodiprion spp., Pogonomyrmex spp., Polistes spp., Solenopsis spp.,Vespula spp., and Xylocopa spp. A non-exhaustive list of particularspecies includes, but is not limited to, Athalla rosae, Atta texana,Iridomyrmex humilis, Monomorium minimum, Monomorium pharaonis,Solenopsis invicta, Solenopsis geminata, Solenopsis molesta, Solenopsisrichtery, Solenopsis xyloni, and Tapinoma sessile.

In another embodiment, the molecules of Formula One may be used tocontrol pests of the Order Isoptera. A non-exhaustive list of particulargenera includes, but is not limited to, Coptotermes spp., Comitermesspp., Cryptotermes spp., Heterotermes spp., Kalotermes spp.,Incisitermes spp., Macrotermes spp., Marginitermes spp., Microcerotermesspp., Procomitermes spp., Reticulitermes spp., Schedorhinotermes spp.,and Zootermopsis spp. A non-exhaustive list of particular speciesincludes, but is not limited to, Coptotermes curvignathus, Coptotermesfrenchi, Coptotermes formosanus, Heterotermes aureus, Microtermes obesi,Reticulitermes banyulensis, Reticulitermes grassei, Reticulitermesflavipes, Reticulitermes hageni, Reticulitermes hesperus, Reticulitermessantonensis, Reticulitermes speratus, Reticulitermes tibialis, andReticulitermes virginicus.

In another embodiment, the molecules of Formula One may be used tocontrol pests of the Order Lepidoptera. A non-exhaustive list ofparticular genera includes, but is not limited to, Adoxophyes spp.,Agrotis spp., Argyrotaenia spp., Cacoecia spp., Caloptilia spp., Chilospp., Chrysodeixis spp., Collas spp., Crambus spp., Diaphania spp.,Diatraea spp., Earias spp., Ephestia spp., Epimecis spp., Feltia spp.,Gortyna spp., Helicoverpa spp., Heliothis spp., Indarbela spp.,Lithocolletis spp., Loxagrotis spp., Malacosoma spp., Peridroma spp.,Phyllonorycter spp., Pseudaletia spp., Sesamia spp., Spodoptera spp.,Synanthedon spp., and Yponomeuta spp. A non-exhaustive list ofparticular species includes, but is not limited to, Achaea janata,Adoxophyes orana, Agrotis ipsilon, Alabama argillacea, Amorbia cuneana,Amyelois transitella, Anacamptodes defectaria, Anarsia lineatella,Anomis sabulifera, Anticarsia gemmatalis, Archips argyrospila, Archipsrosana, Argyrotaenia citrana, Autographa gamma, Bonagota cranaodes,Borbo cinnara, Bucculatrix thurberiella, Capua reticulana, Carposinaniponensis, Chlumetia transversa, Choristoneura rosaceana,Cnaphalocrocis medinalis, Conopomorpha cramerella, Cossus cossus, Cydiacaryana, Cydia funebrana, Cydia molesta, Cydia nigricana, Cydiapomonella, Darna diducta, Diatraea saccharalis, Diatraea grandiosella,Earias insulana, Earias vittella, Ecdytolopha aurantianum, Elasmopalpuslignosellus, Ephestia cautella, Ephestia elutella, Ephestia kuehniella,Epinotia aporema, Epiphyas postvittana, Erionota thrax, Eupoeciliaambiguella, Euxoa auxiliaris, Grapholita molesta, Hedylepta indicata,Helicoverpa armigera, Helicoverpa zea, Heliothis virescens, Hellulaundalis, Keiferia lycopersicella, Leucinodes orbonalis, Leucopteracoffeella, Leucoptera malifoliella, Lobesia botrana, Loxagrotisalbicosta, Lymantria dispar, Lyonetia clerkella, Mahasena corbetti,Mamestra brassicae, Maruca testulalis, Metisa plana, Mythimna unipuncta,Neoleucinodes elegantalis, Nymphula depunctalis, Operophtera brumata,Ostrinia nubilalis, Oxydia vesulia, Pandemis cerasana, Pandemisheparana, Papilio demodocus, Pectinophora gossypiella, Peridroma saucia,Perileucoptera coffeella, Phthorimaea operculella, Phyllocnistiscitrella, Pieris rapae, Plathypena scabra, Plodia interpunctella,Plutella xylostella, Polychrosis viteana, Prays endocarpa, Prays oleae,Pseudaletia unipuncta, Pseudoplusia includens, Rachiplusia nu,Scirpophaga incertulas, Sesamia inferens, Sesamia nonagrioides, Setoranitens, Sitotroga cerealella, Sparganothis pilleriana, Spodopteraexigua, Spodoptera frugiperda, Spodoptera eridania, Thecla basilides,Tineola bisselliella, Trichoplusia ni, Tuta absoluta, Zeuzera coffeae,and Zeuzera pyrina.

In another embodiment, the molecules of Formula One may be used tocontrol pests of the Order Mallophaga. A non-exhaustive list ofparticular genera includes, but is not limited to, Anaticola spp.,Bovicola spp., Chelopistes spp., Goniodes spp., Menacanthus spp., andTrichodectes spp. A non-exhaustive list of particular species includes,but is not limited to, Bovicola bovis, Bovicola caprae, Bovicola ovis,Chelopistes meleagridis, Goniodes dissimilis, Goniodes gigas,Menacanthus stramineus, Menopon gallinae, and Trichodectes canis.

In another embodiment, the molecules of Formula One may be used tocontrol pests of the Order Orthoptera. A non-exhaustive list ofparticular genera includes, but is not limited to, Melanoplus spp., andPterophylla spp. A non-exhaustive list of particular species includes,but is not limited to, Anabrus simplex, Gryllotalpa africana,Gryllotalpa australis, Gryllotalpa brachyptera, Gryllotalpa hexadactyla,Locusta migratoria, Microcentrum retinerve, Schistocerca gregaria, andScudderia furcata.

In another embodiment, the molecules of Formula One may be used tocontrol pests of the Order Siphonaptera. A non-exhaustive list ofparticular species includes, but is not limited to, Ceratophyllusgallinae, Ceratophyllus niger, Ctenocephalides canis, Ctenocephalidesfells, and Pulex irritans.

In another embodiment, the molecules of Formula One may be used tocontrol pests of the Order Thysanoptera. A non-exhaustive list ofparticular genera includes, but is not limited to, Caliothrips spp.,Frankliniella spp., Scirtothrips spp., and Thrips spp. A non-exhaustivelist of particular sp. includes, but is not limited to, Frankliniellafusca, Frankliniella occidentalis, Frankliniella schultzei,Frankliniella williamsi, Heliothrips haemorrhoidalis, Rhipiphorothripscruentatus, Scirtothrips citri, Scirtothrips dorsalis, and Taeniothripsrhopalantennalis, Thrips hawaiiensis, Thrips nigropilosus, Thripsorientalis, Thrips tabaci.

In another embodiment, the molecules of Formula One may be used tocontrol pests of the Order Thysanura. A non-exhaustive list ofparticular genera includes, but is not limited to, Lepisma spp. andThermobia spp.

In another embodiment, the molecules of Formula One may be used tocontrol pests of the Order Acarina. A non-exhaustive list of particulargenera includes, but is not limited to, Acarus spp., Aculops spp.,Boophilus spp., Demodex spp., Dermacentor spp., Epitrimerus spp.,Eriophyes spp., Ixodes spp., Oligonychus spp., Panonychus spp.,Rhizoglyphus spp., and Tetranychus spp. A non-exhaustive list ofparticular species includes, but is not limited to, Acarapis woodi,Acarus siro, Aceria mangiferae, Aculops lycopersici, Aculus pelekassi,Aculus schlechtendali, Amblyomma americanum, Brevipalpus obovatus,Brevipalpus phoenicis, Dermacentor variabilis, Dermatophagoidespteronyssinus, Eotetranychus carpini, Notoedres cati, Oligonychuscoffeae, Oligonychus ilicis, Panonychus citri, Panonychus ulmi,Phyllocoptruta oleivora, Polyphagotarsonemus latus, Rhipicephalussanguineus, Sarcoptes scabiei, Tegolophus perseaflorae, Tetranychusurticae, and Varroa destructor.

In another embodiment, the molecules of Formula One may be used tocontrol pest of the Order Symphyla. A non-exhaustive list of particularsp. includes, but is not limited to, Scutigerella immaculata.

In another embodiment, the molecules of Formula One may be used tocontrol pests of the Phylum Nematoda. A non-exhaustive list ofparticular genera includes, but is not limited to, Aphelenchoides spp.,Belonolaimus spp., Criconemella spp., Ditylenchus spp., Heterodera spp.,Hirschmanniella spp., Hoplolaimus spp., Meloidogyne spp., Pratylenchusspp., and Radopholus spp. A non-exhaustive list of particular sp.includes, but is not limited to, Dirofilaria immitis, Heterodera zeae,Meloidogyne incognita, Meloidogyne javanica, Onchocerca volvulus,Radopholus similis, and Rotylenchulus reniformis.

For additional information consult “HANDBOOK OF PEST CONTROL—THEBEHAVIOR, LIFE HISTORY, AND CONTROL OF HOUSEHOLD PESTS” by ArnoldMallis, 9th Edition, copyright 2004 by GIE Media Inc.

Applications

Controlling pests of Phyla Nematoda, Arthropoda, and/or Molluscagenerally means that pest populations, pest activity, or both, arereduced in an locus. This can come about when:

(a) pest populations are repulsed from a locus;

(b) pests are incapacitated in, or around, a locus; or

(c) pests are exterminated in, or around, a locus.

Of course, a combination of these results can occur. Generally, pestpopulations, activity, or both are desirably reduced more than fiftypercent, preferably more than 90 percent, and most preferably more than98 percent. Generally, the locus is not in, or on, a human;consequently, the locus is generally a non-human locus.

In another embodiment, the locus to which a molecule of Formula One isapplied can be any locus that is inhabited, or that may becomeinhabited, or that may be traversed, by a pest of Phyla Nematoda,Arthropoda, and/or Mollusca. For example, the locus can be:

(a) where crops, trees, fruits, cereals, fodder species, vines, turf,and/or ornamental plants, are growing;

(b) where domesticated animals are residing;

(c) the interior or exterior surfaces of buildings (such as places wheregrains are stored);

(d) the materials of construction used in buildings (such as impregnatedwood); and

(e) the soil around buildings.

Particular crop areas to use a molecule of Formula One include areaswhere apples, corn, sunflowers, cotton, soybeans, canola, wheat, rice,sorghum, barley, oats, potatoes, oranges, alfalfa, lettuce,strawberries, tomatoes, peppers, crucifers, pears, tobacco, almonds,sugar beets, beans and other valuable crops are growing or the seedsthereof are going to be planted. It is also advantageous to use ammoniumsulfate with a molecule of Formula One when growing various plants.

In another embodiment, molecules of Formula One are generally used inamounts from about 0.0001 grams per hectare to about 5000 grams perhectare to provide control. In another embodiment, it is preferred thatmolecules of Formula One are used in amounts from about 0.001 grams perhectare to about 500 grams per hectare. In another embodiment, it ismore preferred that molecules of Formula One are used in amounts fromabout 0.01 gram per hectare to about 50 grams per hectare.

The molecules of Formula One may be used in mixtures, appliedsimultaneously or sequentially, alone or with other compounds to enhanceplant vigor (e.g. to grow a better root system, to better withstandstressful growing conditions). Such other compounds are, for example,compounds that modulate plant ethylene receptors, most notably1-methylcyclopropene (also known as 1-MCP). Furthermore, such moleculesmay be used during times when pest activity is low, such as before theplants that are growing begin to produce valuable agriculturalcommodities. Such times include the early planting season when pestpressure is usually low.

The molecules of Formula One can be applied to the foliar and fruitingportions of plants to control pests. The molecules will either come indirect contact with the pest, or the pest will consume the pesticidewhen eating leaf, fruit mass, or extracting sap, that contains thepesticide. The molecules of Formula One can also be applied to the soil,and when applied in this manner, root and stem feeding pests can becontrolled. The roots can absorb a molecule taking it up into the foliarportions of the plant to control above ground chewing and sap feedingpests.

Generally, with baits, the baits are placed in the ground where, forexample, termites can come into contact with, and/or be attracted to,the bait. Baits can also be applied to a surface of a building,(horizontal, vertical, or slant surface) where, for example, ants,termites, cockroaches, and flies, can come into contact with, and/or beattracted to, the bait. Baits can comprise a molecule of Formula One.

The molecules of Formula One can be encapsulated inside, or placed onthe surface of a capsule. The size of the capsules can range fromnanometer size (about 100-900 nanometers in diameter) to micrometer size(about 10-900 microns in diameter).

Because of the unique ability of the eggs of some pests to resistcertain pesticides, repeated applications of the molecules of FormulaOne may be desirable to control newly emerged larvae.

Systemic movement of pesticides in plants may be utilized to controlpests on one portion of the plant by applying (for example by sprayingan area) the molecules of Formula One to a different portion of theplant. For example, control of foliar-feeding insects can be achieved bydrip irrigation or furrow application, by treating the soil with forexample pre- or post-planting soil drench, or by treating the seeds of aplant before planting.

Seed treatment can be applied to all types of seeds, including thosefrom which plants genetically modified to express specialized traitswill germinate. Representative examples include those expressingproteins toxic to invertebrate pests, such as Bacillus thuringiensis orother insecticidal toxins, those expressing herbicide resistance, suchas “Roundup Ready” seed, or those with “stacked” foreign genesexpressing insecticidal toxins, herbicide resistance,nutrition-enhancement, drought resistance, or any other beneficialtraits. Furthermore, such seed treatments with the molecules of FormulaOne may further enhance the ability of a plant to better withstandstressful growing conditions. This results in a healthier, more vigorousplant, which can lead to higher yields at harvest time. Generally, about1 gram of the molecules of Formula One to about 500 grams per 100,000seeds is expected to provide good benefits, amounts from about 10 gramsto about 100 grams per 100,000 seeds is expected to provide betterbenefits, and amounts from about 25 grams to about 75 grams per 100,000seeds is expected to provide even better benefits.

It should be readily apparent that the molecules of Formula One may beused on, in, or around plants genetically modified to expressspecialized traits, such as Bacillus thuringiensis or other insecticidaltoxins, or those expressing herbicide resistance, or those with“stacked” foreign genes expressing insecticidal toxins, herbicideresistance, nutrition-enhancement, or any other beneficial traits.

The molecules of Formula One may be used for controlling endoparasitesand ectoparasites in the veterinary medicine sector or in the field ofnon-human animal keeping. The molecules of Formula One are applied, suchas by oral administration in the form of, for example, tablets,capsules, drinks, granules, by dermal application in the form of, forexample, dipping, spraying, pouring on, spotting on, and dusting, and byparenteral administration in the form of, for example, an injection.

The molecules of Formula One may also be employed advantageously inlivestock keeping, for example, cattle, sheep, pigs, chickens, andgeese. They may also be employed advantageously in pets such as, horses,dogs, and cats. Particular pests to control would be fleas and ticksthat are bothersome to such animals. Suitable formulations areadministered orally to the animals with the drinking water or feed. Thedosages and formulations that are suitable depend on the species.

The molecules of Formula One may also be used for controlling parasiticworms, especially of the intestine, in the animals listed above.

The molecules of Formula One may also be employed in therapeutic methodsfor human health care. Such methods include, but are limited to, oraladministration in the form of, for example, tablets, capsules, drinks,granules, and by dermal application.

Pests around the world have been migrating to new environments (for suchpest) and thereafter becoming a new invasive species in such newenvironment. The molecules of Formula One may also be used on such newinvasive species to control them in such new environment.

The molecules of Formula One may also be used in an area where plants,such as crops, are growing (e.g. pre-planting, planting, pre-harvesting)and where there are low levels (even no actual presence) of pests thatcan commercially damage such plants. The use of such molecules in sucharea is to benefit the plants being grown in the area. Such benefits,may include, but are not limited to, improving the health of a plant,improving the yield of a plant (e.g. increased biomass and/or increasedcontent of valuable ingredients), improving the vigor of a plant (e.g.improved plant growth and/or greener leaves), improving the quality of aplant (e.g. improved content or composition of certain ingredients), andimproving the tolerance to abiotic and/or biotic stress of the plant.

Before a pesticide can be used or sold commercially, such pesticideundergoes lengthy evaluation processes by various governmentalauthorities (local, regional, state, national, and international).Voluminous data requirements are specified by regulatory authorities andmust be addressed through data generation and submission by the productregistrant or by a third party on the product registrant's behalf, oftenusing a computer with a connection to the World Wide Web. Thesegovernmental authorities then review such data and if a determination ofsafety is concluded, provide the potential user or seller with productregistration approval. Thereafter, in that locality where the productregistration is granted and supported, such user or seller may use orsell such pesticide.

A molecule according to Formula One can be tested to determine itsefficacy against pests. Furthermore, mode of action studies can beconducted to determine if said molecule has a different mode of actionthan other pesticides. Thereafter, such acquired data can bedisseminated, such as by the internet, to third parties.

The headings in this document are for convenience only and must not beused to interpret any portion hereof.

Table Section

TABLE 1 Structure and Preparation Method for C Series Compounds Prep.according to No. Structure Example C1

1 C2

2 C3

3 C4

4 C5

5 C6

5 C7

5 C8

5 C9

5 C10

5 C11

6 C12

6 C13

6 C14

6 C15

6 C16

6 C17

6 C18

6 C19

6 C20

6 C21

6 C22

6 C23

6 C24

6 C25

6 C26

6

TABLE 2 Structure and Preparation Method for F Series Compounds Prep.according to No. Structure example F1

7 F2

7 F3

7 F4

7 F5

7 F6

7 F7

9 F8

7 F9

7 F10

7 F11

7 F12

7 F13

7 F14

7 F15

7 F16

7 F17

7 F18

7 F19

7 F20

7 F21

8 F22

8 F23

10 F24

8 F25

8 F26

8 F27

8 F28

8 F29

8 F30

8 F31

8 F32

8 F33

8 F34

8 F35

8 F36

8 F37

8 F38

8 F39

8 F40

8 F41

8 F42

8 F43

9 F44

9 F45

9

TABLE 3 Analytical Data for Compounds in Table 2 Mp No. (° C.) SOR Mass(m/z) ¹H NMR F1 70-72 [a]_(D) ²⁶ = +53.8 ESIMS m/z (400 MHz, DMSO-d₆) δ11.54 (s, (c = 1.040, 466 1H), 9.42 (s, 1H), 8.17 (d, J = CHCl₃) ([M +H]⁺) 8.6 Hz, 2H), 8.09-8.04 (m, 2H), 7.63 (d, J = 8.7 Hz, 2H), 7.58 (d,J = 8.6 Hz, 2H), 7.53- 7.42 (m, 2H), 7.34-7.32 (m, 3H), 5.43-5.41 (m,1H), 5.39- 5.22 (m, 1H), 4.63 (s, 1H). F2 70-73 [a]_(D) ²⁶ = −45.3 ESIMSm/z (400 MHz, DMSO-d₆) δ 9.43 (s, (c = 1.250, 466 1H), 8.18 (d, J = 8.6Hz, 2H), CHCl₃) ([M + H]⁺) 8.08-8.07 (m, 2H), 7.64 (d, J = 8.8 Hz, 2H),7.59 (d, J = 8.6 Hz, 2H), 7.54-7.45 (m, 4H), 7.43-7.42 (m, 2H), 5.44-5.42 (m, 1H), 5.30-5.23 (m, 1H), 4.64 (s, 1H). F3 190-194 ESIMS m/z (400MHz, DMSO-d₆) δ 9.70 (s, 500 1H), 9.31 (s, 1H), 8.08-7.96 ([M + H]⁺) (m,4H), 7.79-7.76 (m, 2H), 7.62 (d, J = 8.6 Hz, 2H), 7.50- 7.37 (m, 4H),5.27 (s, 1H), 4.68 (t, J = 8.8 Hz, 1H), 4.00-3.98 (m, 1H). F4 199-201ESIMS m/z (400 MHz, DMSO-d₆) δ 9.67 (s, 480 1H), 9.35 (bs, 1H),8.07-7.98 ([M + H]⁺) (m, 4H), 7.89-7.77 (m, 2H), 7.62 (d, J = 8.48 Hz,2H), 7.24- 7.17 (m, 4H), 5.20 (bs, 1H), 4.67-4.65 (m, 1H), 3.96 (s, 1H),2.30 (s, 3H). F5 197-200 ESIMS m/z (400 MHz, DMSO-d₆) δ 9.75 (s, 5341H), 9.36 (s, 1H), 8.07-8.00 ([M + H]⁺) (m, 4H), 7.86-7.79 (m, 2H),7.76-7.58 (m, 6H), 5.37 (s, 1H), 4.73 (t, J = 8.6 Hz, 1H), 4.03 (t, J =7.0 Hz, 1H). F6 200-205 ESIMS m/z (400 MHz, DMSO-d₆) δ 9.64 (s, 496 1H),9.35 (s, 1H), 8.16-7.91 ([M + H]⁺) (m, 4H), 7.89-7.68 (m, 2H), 7.62 (d,J = 8.5 Hz, 2H), 7.26 (d, J = 8.2 Hz, 2H), 7.02-6.80 (m, 2H), 5.18 (s,1H), 4.64 (d, J = 9.2 Hz, 1H), 3.96 (s, 1H), 3.75 (s, 3H). F7 140-142ESIMS m/z (400 MHz, DMSO-d₆) δ 11.36 (s, 466 1H), 9.41 (s, 1H),8.44-7.89 ([M + H]⁺) (m, 4H), 7.83-7.15 (m, 9H), 5.40 (t, J = 8.3 Hz,1H), 5.19 (s, 1H), 4.59 (s, 1H). F8 226-228 ESIMS m/z (400 MHz, DMSO-d₆)δ 9.67 (s, 484 1H), 9.35 (s, 1H), 8.17-7.91 ([M + H]⁺) (m, 4H),7.91-7.65 (m, 2H), 7.62 (d, J = 8.6 Hz, 2H), 7.51- 7.31 (m, 2H), 7.20(t, J = 8.9 Hz, 2H), 5.25 (s, 1H), 4.68 (t, J = 8.6 Hz, 1H), 3.98 (t, J= 7.6 Hz, 1H). F9 118-121 ESIMS m/z (400 MHz, DMSO-d₆) δ 11.44 (s, 5461H), 9.40 (d, J = 1.5 Hz, 1H), ([M + H]⁺) 8.36-7.87 (m, 4H), 7.81- 7.32(m, 8H), 5.39 (t, J = 8.2 Hz, 1H), 5.25-4.98 (m, 1H), 4.51 (s, 1H). F10216-220 ESIMS m/z (400 MHz, DMSO-d₆) δ 9.76 (s, 500 1H), 9.36 (s, 1H),8.15-7.97 ([M + H]⁺) (m, 4H), 7.83 (s, 2H), 7.62 (d, J = 8.6 Hz, 2H),7.51 (ddd, J = 12.1, 7.6, 1.7 Hz, 2H), 7.45- 7.27 (m, 2H), 5.52 (t, J =8.3 Hz, 1H), 4.81 (t, J = 8.7 Hz, 1H), 3.96 (t, J = 7.6 Hz, 1H). F11198-202 ESIMS m/z (400 MHz, DMSO-d₆) δ 9.70 (s, 500 1H), 9.36 (s, 1H),8.18-7.93 ([M + H]⁺) (m, 4H), 7.91-7.71 (m, 2H), 7.62 (d, J = 8.6 Hz,2H), 7.55- 7.24 (m, 4H), 5.26 (d, J = 9.1 Hz, 1H), 4.69 (t, J = 8.7 Hz,1H), 4.01 (t, J = 7.7 Hz, 1H). F12 197-202 ESIMS m/z (400 MHz, DMSO-d₆)δ 9.64 (s, 480 1H), 9.47 (s, 1H), 8.17 (d, J = ([M + H]⁺) 8.3 Hz, 2H),7.98 (dd, J = 14.3, 8.5 Hz, 4H), 7.76 (s, 2H), 7.26 (d, J = 8.2 Hz, 2H),7.07-6.76 (m, 2H), 5.16 (s, 1H), 4.64 (t, J = 8.5 Hz, 1H), 3.97 (s, 1H),3.74 (s, 3H). F13 239-242 ESIMS m/z (400 MHz, DMSO-d₆) δ 9.65 (s, 4641H), 9.48 (s, 1H), 8.18 (d, J = ([M + H]⁺) 8.4 Hz, 2H), 8.10-7.88 (m,4H), 7.78 (s, 2H), 7.34-7.06 (m, 4H), 5.19 (s, 1H), 4.66 (t, J = 8.6 Hz,1H), 3.97 (t, J = 7.5 Hz, 1H), 2.30 (s, 3H). F14 238-241 ESIMS m/z (400MHz, DMSO-d₆) δ 9.68 (s, 450 1H), 9.49 (s, 1H), 8.18 (d, J = ([M + H]⁺)8.4 Hz, 2H), 8.12-7.92 (m, 4H), 7.80 (s, 2H), 7.46-7.09 (m, 5H), 5.24(s, 1H), 4.69 (t, J = 8.5 Hz, 1H), 4.01 (d, J = 8.0 Hz, 1H). F15 226-230ESIMS m/z (400 MHz, DMSO-d₆) δ 9.69 (s, 468 1H), 9.49 (s, 1H), 8.18 (d,J = ([M + H]⁺) 8.4 Hz, 2H), 8.00 (dd, J = 16.7, 8.5 Hz, 4H), 7.79 (s,2H), 7.39 (dd, J = 8.5, 5.6 Hz, 2H), 7.20 (t, J = 8.8 Hz, 2H), 5.26 (s,1H), 4.68 (t, J = 8.6 Hz, 1H), 3.98 (t, J = 7.9 Hz, 1H). F16 138-142ESIMS m/z (400 MHz, DMSO-d₆) δ 9.53 (s, 484 1H), 8.17 (t, J = 9.1 Hz,4H), ([M + H]⁺) 7.99 (d, J = 8.5 Hz, 3H), 7.79- 7.43 (m, 6H), 5.40 (t, J= 8.4 Hz, 1H), 5.13 (s, 1H), 4.51 (s, 1H). F17 187-190 ESIMS m/z (400MHz, DMSO-d₆) δ 9.73 (s, 534 1H), 9.49 (s, 1H), 8.18 (d, J = ([M + H]⁺)8.3 Hz, 2H), 8.11-7.91 (m, 4H), 7.91-7.63 (m, 2H), 7.63- 7.43 (m, 2H),7.38 (d, J = 8.2 Hz, 2H), 5.30 (t, J = 8.0 Hz, 1H), 4.71 (t, J = 8.7 Hz,1H), 4.03 (dd, J = 9.4, 6.0 Hz, 1H). F18 187-191 ESIMS m/z (400 MHz,DMSO-d₆) δ 9.71 (s, 484 1H), 9.48 (s, 1H), 8.17 (d, J = ([M + H]⁺) 8.3Hz, 2H), 7.99 (dd, J = 22.3, 8.4 Hz, 4H), 7.77 (s, 2H), 7.55- 7.23 (m,4H), 5.26 (t, J = 8.2 Hz, 1H), 4.68 (t, J = 8.7 Hz, 1H), 4.00 (t, J =7.5 Hz, 1H). F19 232-236 ESIMS m/z (400 MHz, DMSO-d₆) δ 9.77 (s, 4841H), 9.49 (d, J = 1.3 Hz, 1H), ([M + H]⁺) 8.18 (d, J = 8.3 Hz, 2H),8.12- 8.01 (m, 2H), 7.98 (d, J = 8.4 Hz, 2H), 7.84 (s, 2H), 7.51 (ddt, J= 13.3, 7.7, 1.6 Hz, 2H), 7.45- 7.29 (m, 2H), 5.52 (t, J = 8.0 Hz, 1H),4.81 (dd, J = 9.5, 7.9 Hz, 1H), 3.96 (t, J = 7.6 Hz, 1H). F20 121-125[a]_(D) ²⁵ = +21.0 ESIMS m/z (400 MHz, DMSO-d₆) δ 9.33 (s, (c = 1.160,480 1H), 8.86 (bs, 1H), 8.06-8.04 CHCl₃) ([M + H]⁺) (m, 2H), 7.93 (d, J= 8.7 Hz, 2H), 7.77 (s, 1H), 7.61 (d, J = 8.5 Hz, 2H), 7.42-7.35 (m,4H), 7.25 (d, J = 14.1 Hz, 2H), 4.70-4.67 (m, 1H), 4.34 (4, J = 7.6,1H), 4.25 (t, J = 6.4 Hz, 1H), 2.36-2.22 (m, 1H), 1.73- 1.70 (m, 1H).F21 207-212 ESIMS m/z (400 MHz, DMSO-d₆) δ 9.86- 512 9.61 (m, 1H), 9.34(s, 1H), 8.10- ([M + H]⁺) 8.02 (m, 2H), 8.02-7.95 (m, 2H), 7.90-7.75 (m,2H), 7.67- 7.55 (m, 2H), 7.38-7.27 (m, 2H), 6.98-6.87 (m, 2H), 5.53-5.28 (m, 1H), 3.90-3.57 (m, 4H), 3.18-2.98 (m, 1H). F22 190-194 ESIMSm/z (400 MHz, DMSO-d₆) δ 9.92- 496 9.59 (m, 1H), 9.34 (s, 1H), 8.12-([M + H]⁺) 7.91 (m, 4H), 7.91-7.70 (m, 2H), 7.60 (d, J = 8.5 Hz, 2H),7.30 (d, J = 7.6 Hz, 2H), 7.17 (d, J = 7.6 Hz, 2H), 5.61-5.29 (m, 1H),3.85-3.52 (m, 1H), 3.07 (dd, J = 10.7, 8.1 Hz, 1H), 2.29 (s, 3H). F23201-202 ESIMS m/z (400 MHz, DMSO-d₆) δ 9.78 (s, 482 1H), 9.35 (s, 1H),8.10-7.94 ([M + H]⁺) (m, 4H), 7.84 (d, J = 8.4 Hz, 2H), 7.62 (d, J = 8.5Hz, 2H), 7.41 (dd, J = 20.4, 7.4 Hz, 4H), 7.34-7.23 (m, 1H), 5.60- 5.43(m, 1H), 3.88-3.69 (m, 1H), 3.12 (dd, J = 10.7, 8.1 Hz, 1H). F24 220-221ESIMS m/z (400 MHz, DMSO-d₆) δ 9.80 (s, 500 1H), 9.35 (s, 1H), 8.14-7.94([M + H]⁺) (m, 4H), 7.91-7.76 (m, 2H), 7.62 (d, J = 8.6 Hz, 2H), 7.56-7.40 (m, 2H), 7.20 (t, J = 8.8 Hz, 2H), 5.61-5.40 (m, 1H), 3.88-3.73 (m,1H), 3.10 (dd, J = 10.7, 8.1 Hz, 1H). F25 220-224 ESIMS m/z (400 MHz,DMSO-d₆) δ 9.83 (s, 516 1H), 9.36 (s, 1H), 8.12-7.96 ([M + H]⁺) (m, 4H),7.93-7.72 (m, 2H), 7.62 (d, J = 8.5 Hz, 2H), 7.53- 7.41 (m, 4H),5.59-5.32 (m, 1H), 3.80 (t, J = 9.0 Hz, 1H), 3.10 (dd, J = 10.8, 8.0 Hz,1H). F26 102-106 ESIMS m/z (400 MHz, DMSO-d₆) δ 9.40 (s, 560 1H),8.18-8.01 (m, 5H), 7.62 ([M + H]⁺) (dd, J = 8.4, 5.9 Hz, 6H), 7.44 (d, J= 8.1 Hz, 2H), 5.47 (t, J = 7.6 Hz, 1H), 3.91 (dd, J = 10.7, 8.2 Hz,1H), 3.28 (s, 1H). F27 ESIMS m/z (400 MHz, DMSO-d₆) δ 9.86 (s, 550 1H),9.36 (s, 1H), 8.13-7.93 ([M + H]⁺) (m, 4H), 7.84 (s, 2H), 7.76 (d, J =8.0 Hz, 1H), 7.67 (d, J = 7.4 Hz, 1H), 7.65-7.53 (m, 2H), 7.31 (s, 1H),7.18 (s, 1H), 5.82- 5.31 (m, 1H), 3.97-3.65 (m, 1H), 3.26-3.00 (m, 1H).F28 215-219 ESIMS m/z (400 MHz, DMSO-d₆) δ 9.84 (s, 566 1H), 9.36 (s,1H), 8.13-7.95 ([M + H]⁺) (m, 4H), 7.84 (s, 2H), 7.59 (dd, J = 20.6, 8.4Hz, 4H), 7.38 (d, J = 8.1 Hz, 2H), 5.69-5.43 (m, 1H), 3.83 (d, J = 9.9Hz, 1H), 3.13 (dd, J = 10.8, 8.0 Hz, 1H). F29 141-144 ESIMS m/z (400MHz, DMSO-d₆) δ 9.84 (s, 516 1H), 9.36 (s, 1H), 8.13-7.95 ([M + H]⁺) (m,4H), 7.84 (s, 2H), 7.62 (d, J = 8.5 Hz, 2H), 7.53-7.28 (m, 4H),5.64-5.33 (m, 1H), 3.80 (d, J = 9.0 Hz, 1H), 3.13 (dd, J = 10.8, 8.1 Hz,1H). F30 147-151 ESIMS m/z (400 MHz, DMSO-d₆) δ 9.89 (s, 516 1H), 9.36(d, J = 2.3 Hz, 1H), ([M + H]⁺) 8.04 (dd, J = 16.6, 8.3 Hz, 4H), 7.85(d, J = 8.3 Hz, 2H), 7.62 (d, J = 8.5 Hz, 2H), 7.49 (t, J = 10.9 Hz,2H), 7.41-7.28 (m, 2H), 5.89-5.63 (m, 1H), 3.89 (t, J = 9.4 Hz, 1H),3.09 (dd, J = 11.0, 7.0 Hz, 1H). F31 172-174 ESIMS m/z (400 MHz,DMSO-d₆) δ 9.81 (s, 530 1H), 9.36 (s, 1H), 8.12-7.93 ([M + H]⁺) (m, 4H),7.83 (d, J = 8.6 Hz, 2H), 7.62 (d, J = 8.5 Hz, 2H), 7.41 (t, J = 4.0 Hz,2H), 7.28 (d, J = 8.2 Hz, 1H), 5.45 (s, 1H), 3.79 (d, J = 11.5 Hz, 1H),3.10 (dd, J = 10.8, 8.3 Hz, 1H), 2.35 (s, 3H) F32 225-230 ESIMS m/z (400MHz, DMSO-d₆) δ 9.75 (s, 496 1H), 9.47 (s, 1H), 8.16 (d, J = ([M + H]⁺)8.3 Hz, 2H), 8.09-7.90 (m, 5H), 7.83 (s, 1H), 7.33 (d, J = 8.1 Hz, 2H),6.92 (d, J = 8.2 Hz, 2H), 5.56-5.21 (m, 1H), 3.86-3.62 (m, 4H), 3.07(dd, J = 10.7, 8.1 Hz, 1H). F33 210-214 ESIMS m/z (400 MHz, DMSO-d₆) δ9.76 (s, 480 1H), 9.47 (s, 1H), 8.16 (d, J = ([M + H]⁺) 8.4 Hz, 2H),7.99 (dd, J = 16.5, 8.4 Hz, 5H), 7.83 (s, 1H), 7.31 (d, J = 7.6 Hz, 2H),7.17 (d, J = 7.7 Hz, 2H), 5.44 (s, 1H), 3.75 (s, 1H), 3.08 (dd, J =10.7, 8.1 Hz, 1H), 2.30 (s, 3H). F34 ESIMS m/z (400 MHz, DMSO-d₆) δ 9.78(s, 466 1H), 9.63-9.34 (m, 1H), 8.16 ([M + H]⁺) (d, J = 8.3 Hz, 2H),8.08-7.91 (m, 5H), 7.85 (d, J = 7.2 Hz, 2H), 7.37 (ddd, J = 33.5, 23.2,7.6 Hz, 6H), 5.49 (s, 1H), 3.79 (s, 1H), 3.21-2.99 (m, 1H). F35 209-214ESIMS m/z (400 MHz, DMSO-d₆) δ 9.82 (s, 484 1H), 9.49 (s, 1H), 8.17 (d,J = ([M + H]⁺) 8.3 Hz, 2H), 8.09-7.94 (m, 4H), 7.84 (s, 2H), 7.48 (dd, J= 8.3, 5.4 Hz, 2H), 7.20 (t, J = 8.7 Hz, 2H), 5.50 (s, 1H), 3.89- 3.67(m, 1H), 3.10 (dd, J = 10.8, 8.1 Hz, 1H). F36 231-236 ESIMS m/z (400MHz, DMSO-d₆) δ 9.82 (s, 500 1H), 9.47 (s, 1H), 8.16 (d, J = ([M + H]⁺)8.3 Hz, 2H), 8.08-7.91 (m, 4H), 7.83 (s, 1H), 7.45 (t, J = 6.3 Hz, 5H),5.49 (s, 1H), 3.78 (d, J = 8.7 Hz, 1H), 3.09 (dd, J = 10.8, 8.0 Hz, 1H).F37 64-67 ESIMS m/z (400 MHz, DMSO-d₆) δ 9.54 (s, 545 1H), 8.16 (dd, J =19.9, 8.3 Hz, ([M + 2]⁺) 4H), 8.00 (d, J = 8.4 Hz, 2H), 7.75-7.58 (m,5H), 7.45 (d, J = 8.1 Hz, 2H), 5.48 (t, J = 7.6 Hz, 1H), 4.05-3.82 (m,1H), 3.32 (s, 1H). F38 ESIMS m/z (400 MHz, DMSO-d₆) δ 9.88 (s, 534 1H),9.49 (s, 1H), 8.18 (d, J = ([M + H]⁺) 8.4 Hz, 2H), 8.09-7.92 (m, 4H),7.86 (s, 1H), 7.76 (d, J = 8.1 Hz, 1H), 7.67 (d, J = 8.1 Hz, 1H), 7.59(s, 1H), 7.31 (d, J = 7.9 Hz, 1H), 7.20-7.13 (m, 1H), 5.76-5.48 (m, 1H),4.03- 3.75 (m, 1H), 3.24-3.03 (m, 1H). F39 223-228 ESIMS m/z (400 MHz,DMSO-d₆) δ 9.83 (s, 550 1H), 9.47 (s, 1H), 8.16 (d, J = ([M + H]⁺) 8.4Hz, 2H), 7.99 (dd, J = 21.5, 8.4 Hz, 4H), 7.83 (s, 2H), 7.56 (d, J = 8.2Hz, 2H), 7.37 (d, J = 8.1 Hz, 2H), 5.52 (s, 1H), 3.88- 3.73 (m, 1H),3.12 (dd, J = 10.8, 8.0 Hz, 1H). F40 198-201 ESIMS m/z (400 MHz,DMSO-d₆) δ 9.86 (s, 500 1H), 9.49 (s, 1H), 8.18 (d, J = ([M + H]⁺) 8.4Hz, 2H), 8.12-7.94 (m, 4H), 7.85 (s, 2H), 7.62-7.33 (m, 4H), 5.52 (s,1H), 3.83 (d, J = 10.1 Hz, 1H), 3.14 (dd, J = 10.8, 8.1 Hz, 1H). F41195-199 ESIMS m/z (400 MHz, DMSO-d₆) δ 9.91 (s, 500 1H), 9.49 (s, 1H),8.18 (d, J = ([M + H]⁺) 8.3 Hz, 2H), 8.10-7.93 (m, 4H), 7.87 (d, J = 8.2Hz, 2H), 7.60-7.43 (m, 2H), 7.36 (dd, J = 7.1, 3.0 Hz, 2H), 5.76 (s,1H), 3.89 (dd, J = 10.9, 7.9 Hz, 1H), 3.09 (dd, J = 10.9, 6.9 Hz, 1H).F42 191-197 ESIMS m/z (400 MHz, DMSO-d₆) δ 9.82 (s, 514 1H), 9.49 (d, J= 1.8 Hz, 1H), ([M + H]⁺) 8.18 (d, J = 8.3 Hz, 2H), 8.09- 7.92 (m, 4H),7.84 (s, 2H), 7.49- 7.35 (m, 2H), 7.28 (d, J = 8.2 Hz, 1H), 5.45 (s,1H), 3.78 (s, 1H), 3.10 (dd, J = 10.8, 8.2 Hz, 1H), 2.35 (s, 3H) F43138-140 ESIMS m/z (400 MHz, DMSO-d₆) δ 9.32 (s, 514 1H), 8.91 (s, 1H),8.04 (d, J = ([M + H]⁺) 4.96 Hz, 2H), 7.93 (d, J = 8.76 Hz, 2H),7.78-7.77 (m, 2H), 7.60 (d, J = 8.56 Hz, 2H), 7.46- 7.35 (m, 4H),4.70-4.66 (m, 1H), 4.35-4.30 (m, 1H), 4.24 (t, J = 6.44 Hz, 1H),2.27-2.23 (m, 1H), 1.68-1.66 (m, 1H). F44 89-92 ESIMS m/z (400 MHz,DMSO-d₆) δ 9.33 (s, 494 1H), 8.07-8.02 (m, 3H), 7.95- ([M + H]⁺) 7.90(m, 2H), 7.73-7.72 (m, 2H), 7.61-7.59 (m, 3H), 7.28- 7.26 (m, 1H),7.17-7.15 (m, 2H), 4.63-4.62 (m, 1H), 4.31- 4.29 (m, 1H), 4.21 (t, J =6.12 Hz, 1H), 2.29-2.19 (m, 1H), 1.69-1.67 (m, 1H). F45 154-157 (400MHz, DMSO-d₆) δ 9.33 (s, 1H), 8.91 (s, 1H), 8.91-8.03 (m, 2H), 7.94 (d,J = 8.7 Hz, 2H), 7.78 (s, 1H), 7.74 (d, J = 8.3 Hz, 2H), 7.65 (d, J =8.0 Hz, 2H), 7.60 (d, J = 8.8 Hz, 2H), 4.80-4.77 (m, 1H), 4.39- 4.33 (m,1H), 4.28-4.25 (m, 1H), 2.32-2.27 (m, 1H), 1.75- 1.68 (m, 1H).

BAW and CL Rating Table % Control (or Mortality) Rating 50-100 A Morethan 0-Less than 50 B Not Tested C No activity noticed in this bioassayD

GPA & YFM Rating Table % Control (or Mortality) Rating 80-100 A Morethan 0-Less than 80 B Not Tested C No activity noticed in this bioassayD

TABLE ABC Biological Results Insect species No. BAW CL GPA YFM F1 A A AB F2 A A A B F3 A A B C F4 D A D C F5 A A A B F6 A A D C F7 A A A C F8 AA B C F9 A A A C F10 D A D C F11 A A D D F12 D D D C F13 D D D C F14 D DD C F15 A A D C F16 A A A C F17 A A D C F18 A A D C F19 D A D C F20 D AA B F21 A D D C F22 D D D C F23 D D D C F24 B B D C F25 D D D C F26 D BD C F27 D A D C F28 B D D C F29 A A D C F30 A A D C F31 A A D C F32 D DD C F33 D D B C F34 A A D C F35 D A D C F36 D A D C F37 D D D C F38 B AD C F39 D D D C F40 A A B C F41 A A D C F42 D D D C F43 B A A B F44 B AA B F45 A A A B

We claim:
 1. A molecule of the following formula

wherein: (A) R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁹, and R¹⁰ are, eachindependently, H, F, Cl, Br, I, CN, NO₂, OH, (C₁-C₄)alkyl,(C₂-C₄)alkenyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, or(C₃-C₆)cycloalkyl, wherein each alkyl, alkenyl, haloalkyl, alkoxy,haloalkoxy, and cycloalkyl, is optionally substituted with one or moresubstituents, wherein each substituent is independently H, F, Cl, Br, I,CN, NO₂, OH, (C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₁-C₄)haloalkyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, or (C₃-C₆)cycloalkyl; (B) R⁸ is H; (C)L is a linker that is C₁-C₄ alkyl, C₂-C₄ alkenyl, or C₁-C₄ haloalkyl,wherein each alkyl, alkenyl, and haloalkyl, is optionally substitutedwith one or more substituents, wherein each substituent is independentlyF, Cl, CN, OH, or oxo; (D) R¹¹, R¹², R¹³, R¹⁴, and R¹⁵ are, eachindependently, H, F, Cl, Br, I, CN, NO₂, OH, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, or (C₁-C₄)haloalkoxy, wherein eachalkyl, alkoxy, and haloalkyl, is optionally substituted with one or moresubstituents, wherein each substituent is independently F, Cl, CN, OH,or oxo; and (E) Q is O or S.
 2. A molecule according to claim 1 whereinR¹, R², R³, R⁴, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹⁴, and R¹⁵ are H.
 3. A moleculeaccording to claim 1 wherein R⁵ is CF₃ or OCF₃.
 4. A molecule accordingto claim 1 wherein Q is O.
 5. A molecule according to claim 1 wherein Lis —CH₂— or —CH₂CH₂—.
 6. A molecule according to claim 1 wherein R¹¹,R¹², and R¹³ is H, F, Cl, Br, or I.
 7. A molecule according to claim 1wherein R¹² is CH₃.
 8. A molecule according to claim 1 wherein R¹³ isCH₃, OCH₃, CF₃, or OCF₃.
 9. A molecule according to claim 1 wherein: (A)R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁹, and R¹⁰ are, each independently, H,C₁-C₄ haloalkyl, or C₁-C₄ haloalkoxy; (B) R⁶ is H; (C) L is a linkerthat is C₁-C₄ alkyl; (D) R¹¹, R¹², R¹³, R¹⁴, and R¹⁵ are, eachindependently, H, F, Cl, Br, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy,or C₁-C₄ haloalkoxy; and (E) Q is selected from O or S.
 10. A moleculeaccording to claim 1 wherein: (A) R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁹, andR¹⁰ are, each independently, H, C₁-C₄ haloalkyl, or C₁-C₄ haloalkoxy;(B) R⁶ is H; (C) L is a linker that is C₁-C₄ alkyl; (D) R¹¹, R¹², R¹³,R¹⁴, and R¹⁵ are, each independently, H, Cl, Br, C₁-C₄ haloalkyl, orC₁-C₄ haloalkoxy; and (E) Q is O.
 11. A molecule according to claim 1wherein said molecule is selected from one of the following moleculesNo. Structure F1

F2

F3

F4

F5

F6

F7

F8

F9

F11

F15

F16

F17

F18

F29

F30

F31

F34

F40

F41

F45


12. A pesticidal composition comprising a molecule according to claim 1and a carrier.
 13. A pesticidal composition according to claim 12further comprising one or more compounds having a mode of actionselected from: Acetylcholinesterase (AChE) inhibitors; GABA-gatedchloride channel antagonists; Sodium channel modulators; Nicotinicacetylcholine (nAChR) agonists; Nicotinic acetylcholine receptor (nAChR)allosteric activators; Chloride channel activators; Juvenile hormonemimics; Miscellaneous non-specific (multi-site) inhibitors; Selectivehomopteran feeding blockers; Mite growth inhibitors; Microbialdisruptors of insect midgut membranes; Inhibitors of mitochondrial ATPsynthase; Uncouplers of oxidative phosphorylation via disruption of theproton gradient; Nicotinic acetylcholine receptor (nAChR) channelblockers; Inhibitors of chitin biosynthesis, type 0; Inhibitors ofchitin biosynthesis, type 1; Moulting disruptor, Dipteran; Ecdysonereceptor agonists; Octopamine receptor agonists; Mitochondrial complexIII electron transport inhibitors; Mitochondrial complex I electrontransport inhibitors; Voltage-dependent sodium channel blockers;Inhibitors of acetyl CoA carboxylase; Mitochondrial complex IV electrontransport inhibitors; Mitochondrial complex II electron transportinhibitors; and Ryanodine receptor modulators.
 14. A pesticidalcomposition according to claim 12 further comprising one or morecompounds having acaricidal, algicidal, avicidal, bactericidal,fungicidal, herbicidal, insecticidal, molluscicidal, nematicidal,rodenticidal, and/or virucidal properties.
 15. A pesticidal compositionaccording to claim 12 further comprising one or more compounds that areantifeedants, bird repellents, chemosterilants, herbicide safeners,insect attractants, insect repellents, mammal repellents, matingdisrupters, plant activators, plant growth regulators, and/orsynergists.
 16. A pesticidal composition according to claim 12 furthercomprising one or more of the followingcompounds—(3-ethoxypropyl)mercury bromide, 1,2-dichloropropane,1,3-dichloropropene, 1-methylcyclopropene, 1-naphthol,2-(octylthio)ethanol, 2,3,5-tri-iodobenzoic acid, 2,3,6-TBA,2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA-potassium,2,3,6-TBA-sodium, 2,4,5-T, 2,4,5-T-2-butoxypropyl, 2,4,5-T-2-ethylhexyl,2,4,5-T-3-butoxypropyl, 2,4,5-TB, 2,4,5-T-butometyl, 2,4,5-T-butotyl,2,4,5-T-butyl, 2,4,5-T-isobutyl, 2,4,5-T-isoctyl, 2,4,5-T-isopropyl,2,4,5-T-methyl, 2,4,5-T-pentyl, 2,4,5-T-sodium,2,4,5-T-triethylammonium, 2,4,5-T-trolamine, 2,4-D,2,4-D-2-butoxypropyl, 2,4-D-2-ethylhexyl, 2,4-D-3-butoxypropyl,2,4-D-ammonium, 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethylammonium,2,4-DB-isoctyl, 2,4-DB-potassium, 2,4-DB-sodium, 2,4-D-butotyl,2,4-D-butyl, 2,4-D-diethylammonium, 2,4-D-dimethylammonium,2,4-D-diolamine, 2,4-D-dodecylammonium, 2,4-DEB, 2,4-DEP, 2,4-D-ethyl,2,4-D-heptylammonium, 2,4-D-isobutyl, 2,4-D-isoctyl, 2,4-D-isopropyl,2,4-D-isopropylammonium, 2,4-D-lithium, 2,4-D-meptyl, 2,4-D-methyl,2,4-D-octyl, 2,4-D-pentyl, 2,4-D-potassium, 2,4-D-propyl, 2,4-D-sodium,2,4-D-tefuryl, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium,2,4-D-tris(2-hydroxypropyl)ammonium, 2,4-D-trolamine, 2iP,2-methoxyethylmercury chloride, 2-phenylphenol, 3,4-DA, 3,4-DB, 3,4-DP,4-aminopyridine, 4-CPA, 4-CPA-diolamine, 4-CPA-potassium, 4-CPA-sodium,4-CPB, 4-CPP, 4-hydroxyphenethyl alcohol, 8-hydroxyquinoline sulfate,8-phenylmercurioxyquinoline, abamectin, abscisic acid, ACC, acephate,acequinocyl, acetamiprid, acethion, acetochlor, acetophos, acetoprole,acibenzolar, acibenzolar-S-methyl, acifluorfen, acifluorfen-methyl,acifluorfen-sodium, aclonifen, acrep, acrinathrin, acrolein,acrylonitrile, acypetacs, acypetacs-copper, acypetacs-zinc,afidopyropen, afoxolaner, alachlor, alanycarb, albendazole, aldicarb,aldimorph, aldoxycarb, aldrin, allethrin, allicin, allidochlor,allosamidin, alloxydim, alloxydim-sodium, allyl alcohol, allyxycarb,alorac, alpha-cypermethrin, alpha-endosulfan, ametoctradin, ametridione,ametryn, amibuzin, amicarbazone, amicarthiazol, amidithion, amidoflumet,amidosulfuron, aminocarb, aminocyclopyrachlor,aminocyclopyrachlor-methyl, aminocyclopyrachlor-potassium, aminopyralid,aminopyralid-potassium, aminopyralid-tris(2-hydroxypropyl)ammonium,amiprofos-methyl, amiprophos, amisulbrom, amiton, amiton oxalate,amitraz, amitrole, ammonium sulfamate, ammonium α-naphthaleneacetate,amobam, ampropylfos, anabasine, anabasine sulfate, ancymidol, anilazine,anilofos, anisuron, anthraquinone, antu, apholate, aramite, arsenousoxide, asomate, aspirin, asulam, asulam-potassium, asulam-sodium,athidathion, atraton, atrazine, aureofungin, aviglycine, aviglycinehydrochloride, azaconazole, azadirachtin, azafenidin, azamethiphos,azimsulfuron, azinphos-ethyl, azinphos-methyl, aziprotryne, azithiram,azobenzene, azocyclotin, azothoate, azoxystrobin, bachmedesh, barban,barium hexafluorosilicate, barium polysulfide, barthrin, BCPC,beflubutamid, benalaxyl, benalaxyl-M, benazolin,benazolin-dimethylammonium, benazolin-ethyl, benazolin-potassium,bencarbazone, benclothiaz, bendiocarb, benfluralin, benfuracarb,benfuresate, benodanil, benomyl, benoxacor, benoxafos, benquinox,bensulfuron, bensulfuron-methyl, bensulide, bensultap, bentaluron,bentazone, bentazone-sodium, benthiavalicarb, benthiavalicarb-isopropyl,benthiazole, bentranil, benzadox, benzadox-ammonium, benzalkoniumchloride, benzamacril, benzamacril-isobutyl, benzamorf, benzfendizone,benzipram, benzobicyclon, benzofenap, benzofluor, benzohydroxamic acid,benzovindiflupyr, benzoximate, benzoylprop, benzoylprop-ethyl,benzthiazuron, benzyl benzoate, benzyladenine, berberine, berberinechloride, beta-cyfluthrin, beta-cypermethrin, bethoxazin, bicyclopyrone,bifenazate, bifenox, bifenthrin, bifujunzhi, bilanafos,bilanafos-sodium, binapacryl, bingqingxiao, bioallethrin,bioethanomethrin, biopermethrin, bioresmethrin, biphenyl, bisazir,bismerthiazol, bispyribac, bispyribac-sodium, bistrifluron, bitertanol,bithionol, bixafen, blasticidin-S, borax, Bordeaux mixture, boric acid,boscalid, brassinolide, brassinolide-ethyl, brevicomin, brodifacoum,brofenvalerate, brofluthrinate, bromacil, bromacil-lithium,bromacil-sodium, bromadiolone, bromethalin, bromethrin, bromfenvinfos,bromoacetamide, bromobonil, bromobutide, bromocyclen, bromo-DDT,bromofenoxim, bromophos, bromophos-ethyl, bromopropylate, bromothalonil,bromoxynil, bromoxynil butyrate, bromoxynil heptanoate, bromoxyniloctanoate, bromoxynil-potassium, brompyrazon, bromuconazole, bronopol,bucarpolate, bufencarb, buminafos, bupirimate, buprofezin, Burgundymixture, busulfan, butacarb, butachlor, butafenacil, butamifos,butathiofos, butenachlor, butethrin, buthidazole, buthiobate, buthiuron,butocarboxim, butonate, butopyronoxyl, butoxycarboxim, butralin,butroxydim, buturon, butylamine, butylate, cacodylic acid, cadusafos,cafenstrole, calcium arsenate, calcium chlorate, calcium cyanamide,calcium polysulfide, calvinphos, cambendichlor, camphechlor, camphor,captafol, captan, carbamorph, carbanolate, carbaryl, carbasulam,carbendazim, carbendazim benzenesulfonate, carbendazim sulfite,carbetamide, carbofuran, carbon disulfide, carbon tetrachloride,carbophenothion, carbosulfan, carboxazole, carboxide, carboxin,carfentrazone, carfentrazone-ethyl, carpropamid, cartap, cartaphydrochloride, carvacrol, carvone, CDEA, cellocidin, CEPC, ceralure,Cheshunt mixture, chinomethionat, chitosan, chlobenthiazone,chlomethoxyfen, chloralose, chloramben, chloramben-ammonium,chloramben-diolamine, chloramben-methyl, chloramben-methylammonium,chloramben-sodium, chloramine phosphorus, chloramphenicol,chloraniformethan, chloranil, chloranocryl, chlorantraniliprole,chlorazifop, chlorazifop-propargyl, chlorazine, chlorbenside,chlorbenzuron, chlorbicyclen, chlorbromuron, chlorbufam, chlordane,chlordecone, chlordimeform, chlordimeform hydrochloride,chlorempenthrin, chlorethoxyfos, chloreturon, chlorfenac,chlorfenac-ammonium, chlorfenac-sodium, chlorfenapyr, chlorfenazole,chlorfenethol, chlorfenprop, chlorfenson, chlorfensulphide,chlorfenvinphos, chlorfluazuron, chlorflurazole, chlorfluren,chlorfluren-methyl, chlorflurenol, chlorflurenol-methyl, chloridazon,chlorimuron, chlorimuron-ethyl, chlormephos, chlormequat, chlormequatchloride, chlornidine, chlornitrofen, chlorobenzilate,chlorodinitronaphthalenes, chloroform, chloromebuform, chloromethiuron,chloroneb, chlorophacinone, chlorophacinone-sodium, chloropicrin,chloropon, chloropropylate, chlorothalonil, chlorotoluron, chloroxuron,chloroxynil, chlorphonium, chlorphonium chloride, chlorphoxim,chlorprazophos, chlorprocarb, chlorpropham, chlorpyrifos,chlorpyrifos-methyl, chlorquinox, chlorsulfuron, chlorthal,chlorthal-dimethyl, chlorthal-monomethyl, chlorthiamid, chlorthiophos,chlozolinate, choline chloride, cholecalciferol, chromafenozide, cinerinI, cinerin II, cinerins, cinidon-ethyl, cinmethylin, cinosulfuron,ciobutide, cisanilide, cismethrin, clacyfos, clethodim, climbazole,cliodinate, clodinafop, clodinafop-propargyl, cloethocarb, clofencet,clofencet-potassium, clofentezine, clofibric acid, clofop,clofop-isobutyl, clomazone, clomeprop, cloprop, cloproxydim, clopyralid,clopyralid-methyl, clopyralid-olamine, clopyralid-potassium,clopyralid-tris(2-hydroxypropyl)ammonium, cloquintocet,cloquintocet-mexyl, cloransulam, cloransulam-methyl, closantel,clothianidin, clotrimazole, cloxyfonac, cloxyfonac-sodium, CMA,codlelure, colophonate, copper acetate, copper acetoarsenite, copperarsenate, copper carbonate, basic, copper hydroxide, copper naphthenate,copper oleate, copper oxychloride, copper silicate, copper sulfate,copper zinc chromate, coumachlor, coumafuryl, coumaphos, coumatetralyl,coumithoate, coumoxystrobin, coumoxystrobin, CPMC, CPMF, CPPC,credazine, cresol, crimidine, crotamiton, crotoxyphos, crufomate,cryolite, cue-lure, cufraneb, cumyluron, cuprobam, cuprous oxide,curcumenol, cyanamide, cyanatryn, cyanazine, cyanofenphos, cyanophos,cyanthoate, cyantraniliprole, cyazofamid, cybutryne, cyclafuramid,cyclanilide, cyclaniliprole, cyclethrin, cycloate, cycloheximide,cycloprate, cycloprothrin, cyclopyrimorate, cyclosulfamuron,cycloxaprid, cycloxydim, cycluron, cyenopyrafen, cyflufenamid,cyflumetofen, cyfluthrin, cyhalofop, cyhalofop-butyl, cyhalothrin,cyhexatin, cymiazole, cymiazole hydrochloride, cymoxanil, cyometrinil,cypendazole, cypermethrin, cyperquat, cyperquat chloride, cyphenothrin,cyprazine, cyprazole, cyproconazole, cyprodinil, cyprofuram, cypromid,cyprosulfamide, cyromazine, cythioate, daimuron, dalapon,dalapon-calcium, dalapon-magnesium, dalapon-sodium, daminozide,dayoutong, dazomet, dazomet-sodium, DBCP, d-camphor, DCIP, DCPTA, DDT,debacarb, decafentin, decarbofuran, dehydroacetic acid, delachlor,deltamethrin, demephion, demephion-O, demephion-S, demeton,demeton-methyl, demeton-O, demeton-O-methyl, demeton-S,demeton-S-methyl, demeton-S-methylsulphon, desmedipham, desmetryn,d-fanshiluquebingjuzhi, diafenthiuron, dialifos, di-allate, diamidafos,diatomaceous earth, diazinon, dibutyl phthalate, dibutyl succinate,dicamba, dicamba-diglycolamine, dicamba-dimethylammonium,dicamba-diolamine, dicamba-isopropylammonium, dicamba-methyl,dicamba-olamine, dicamba-potassium, dicamba-sodium, dicamba-trolamine,dicapthon, dichlobenil, dichlofenthion, dichlofluanid, dichlone,dichloralurea, dichlorbenzuron, dichlorflurenol, dichlorflurenol-methyl,dichlormate, dichlormid, dichlorophen, dichlorprop,dichlorprop-2-ethylhexyl, dichlorprop-butotyl,dichlorprop-dimethylammonium, dichlorprop-ethylammonium,dichlorprop-isoctyl, dichlorprop-methyl, dichlorprop-P,dichlorprop-P-2-ethylhexyl, dichlorprop-P-dimethylammonium,dichlorprop-potassium, dichlorprop-P-potassium, dichlorprop-P-sodium,dichlorprop-sodium, dichlorvos, dichlozoline, diclobutrazol, diclocymet,diclofop, diclofop-methyl, diclomezine, diclomezine-sodium, dicloran,diclosulam, dicofol, dicoumarol, dicresyl, dicrotophos, dicyclanil,dicyclonon, dieldrin, dienochlor, diethamquat, diethamquat dichloride,diethatyl, diethatyl-ethyl, diethofencarb, dietholate, diethylpyrocarbonate, diethyltoluamide, difenacoum, difenoconazole,difenopenten, difenopenten-ethyl, difenoxuron, difenzoquat, difenzoquatmetilsulfate, difethialone, diflovidazin, diflubenzuron, diflufenican,diflufenzopyr, diflufenzopyr-sodium, diflumetorim, dikegulac,dikegulac-sodium, dilor, dimatif, dimefluthrin, dimefox, dimefuron,dimepiperate, dimetachlone, dimetan, dimethacarb, dimethachlor,dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimethirimol,dimethoate, dimethomorph, dimethrin, dimethyl carbate, dimethylphthalate, dimethylvinphos, dimetilan, dimexano, dimidazon,dimoxystrobin, dinex, dinex-diclexine, dingjunezuo, diniconazole,diniconazole-M, dinitramine, dinobuton, dinocap, dinocap-4, dinocap-6,dinocton, dinofenate, dinopenton, dinoprop, dinosam, dinoseb, dinosebacetate, dinoseb-ammonium, dinoseb-diolamine, dinoseb-sodium,dinoseb-trolamine, dinosulfon, dinotefuran, dinoterb, dinoterb acetate,dinoterbon, diofenolan, dioxabenzofos, dioxacarb, dioxathion,diphacinone, diphacinone-sodium, diphenamid, diphenyl sulfone,diphenylamine, dipropalin, dipropetryn, dipyrithione, diquat, diquatdibromide, disparlure, disul, disulfiram, disulfoton, disul-sodium,ditalimfos, dithianon, dithicrofos, dithioether, dithiopyr, diuron,d-limonene, DMPA, DNOC, DNOC-ammonium, DNOC-potassium, DNOC-sodium,dodemorph, dodemorph acetate, dodemorph benzoate, dodicin, dodicinhydrochloride, dodicin-sodium, dodine, dofenapyn, dominicalure,doramectin, drazoxolon, DSMA, dufulin, EBEP, EBP, ecdysterone,edifenphos, eglinazine, eglinazine-ethyl, emamectin, emamectin benzoate,EMPC, empenthrin, endosulfan, endothal, endothal-diammonium,endothal-dipotassium, endothal-disodium, endothion, endrin,enestroburin, enoxastrobin, EPN, epocholeone, epofenonane,epoxiconazole, eprinomectin, epronaz, EPTC, erbon, ergocalciferol,erlujixiancaoan, esdepallethrine, esfenvalerate, esprocarb, etacelasil,etaconazole, etaphos, etem, ethaboxam, ethachlor, ethalfluralin,ethametsulfuron, ethametsulfuron-methyl, ethaprochlor, ethephon,ethidimuron, ethiofencarb, ethiolate, ethion, ethiozin, ethiprole,ethirimol, ethoate-methyl, ethofumesate, ethohexadiol, ethoprophos,ethoxyfen, ethoxyfen-ethyl, ethoxyquin, ethoxysulfuron, ethychlozate,ethyl formate, ethyl α-naphthaleneacetate, ethyl-DDD, ethylene, ethylenedibromide, ethylene dichloride, ethylene oxide, ethylicin, ethylmercury2,3-dihydroxypropyl mercaptide, ethylmercury acetate, ethylmercurybromide, ethylmercury chloride, ethylmercury phosphate, etinofen,etnipromid, etobenzanid, etofenprox, etoxazole, etridiazole, etrimfos,eugenol, EXD, famoxadone, famphur, fenamidone, fenaminosulf,fenaminstrobin, fenamiphos, fenapanil, fenarimol, fenasulam, fenazaflor,fenazaquin, fenbuconazole, fenbutatin oxide, fenchlorazole,fenchlorazole-ethyl, fenchlorphos, fenclorim, fenethacarb, fenfluthrin,fenfuram, fenhexamid, fenitropan, fenitrothion, fenjuntong, fenobucarb,fenoprop, fenoprop-3-butoxypropyl, fenoprop-butometyl, fenoprop-butotyl,fenoprop-butyl, fenoprop-isoctyl, fenoprop-methyl, fenoprop-potassium,fenothiocarb, fenoxacrim, fenoxanil, fenoxaprop, fenoxaprop-ethyl,fenoxaprop-P, fenoxaprop-P-ethyl, fenoxasulfone, fenoxycarb,fenpiclonil, fenpirithrin, fenpropathrin, fenpropidin, fenpropimorph,fenpyrazamine, fenpyroximate, fenquinotrione, fenridazon,fenridazon-potassium, fenridazon-propyl, fenson, fensulfothion,fenteracol, fenthiaprop, fenthiaprop-ethyl, fenthion, fenthion-ethyl,fentin, fentin acetate, fentin chloride, fentin hydroxide, fentrazamide,fentrifanil, fenuron, fenuron TCA, fenvalerate, ferbam, ferimzone,ferrous sulfate, fipronil, flamprop, flamprop-isopropyl, flamprop-M,flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron,flocoumafen, flometoquin, flonicamid, florasulam, fluacrypyrim,fluazifop, fluazifop-butyl, fluazifop-methyl, fluazifop-P,fluazifop-P-butyl, fluazinam, fluazolate, fluazuron, flubendiamide,flubenzimine, flucarbazone, flucarbazone-sodium, flucetosulfuron,fluchloralin, flucofuron, flucycloxuron, flucythrinate, fludioxonil,fluenetil, fluensulfone, flufenacet, flufenerim, flufenican,flufenoxuron, flufenoxystrobin, flufenprox, flufenpyr, flufenpyr-ethyl,flufiprole, fluhexafon, flumethrin, flumetover, flumetralin,flumetsulam, flumezin, flumiclorac, flumiclorac-pentyl, flumioxazin,flumipropyn, flumorph, fluometuron, fluopicolide, fluopyram,fluorbenside, fluoridamid, fluoroacetamide, fluorodifen, fluoroglycofen,fluoroglycofen-ethyl, fluoroimide, fluoromidine, fluoronitrofen,fluothiuron, fluotrimazole, fluoxastrobin, flupoxam, flupropacil,flupropadine, flupropanate, flupropanate-sodium, flupyradifurone,flupyrsulfuron, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium,fluquinconazole, fluralaner, flurazole, flurenol, flurenol-butyl,flurenol-methyl, fluridone, flurochloridone, fluroxypyr,fluroxypyr-butometyl, fluroxypyr-meptyl, flurprimidol, flursulamid,flurtamone, flusilazole, flusulfamide, fluthiacet, fluthiacet-methyl,flutianil, flutolanil, flutriafol, fluvalinate, fluxapyroxad,fluxofenim, folpet, fomesafen, fomesafen-sodium, fonofos, foramsulfuron,forchlorfenuron, formaldehyde, formetanate, formetanate hydrochloride,formothion, formparanate, formparanate hydrochloride, fosamine,fosamine-ammonium, fosetyl, fosetyl-aluminium, fosmethilan, fospirate,fosthiazate, fosthietan, frontalin, fuberidazole, fucaojing, fucaomi,funaihecaoling, fuphenthiourea, furalane, furalaxyl, furamethrin,furametpyr, furathiocarb, furcarbanil, furconazole, furconazole-cis,furethrin, furfural, furilazole, furmecyclox, furophanate, furyloxyfen,gamma-cyhalothrin, gamma-HCH, genit, gibberellic acid, gibberellins,gliftor, glufosinate, glufosinate-ammonium, glufosinate-P,glufosinate-P-ammonium, glufosinate-P-sodium, glyodin, glyoxime,glyphosate, glyphosate-diammonium, glyphosate-dimethylammonium,glyphosate-isopropylammonium, glyphosate-monoammonium,glyphosate-potassium, glyphosate-sesquisodium, glyphosate-trimesium,glyphosine, gossyplure, grandlure, griseofulvin, guazatine, guazatineacetates, halacrinate, halauxifen, halauxifen-methyl, halfenprox,halofenozide, halosafen, halosulfuron, halosulfuron-methyl, haloxydine,haloxyfop, haloxyfop-etotyl, haloxyfop-methyl, haloxyfop-P,haloxyfop-P-etotyl, haloxyfop-P-methyl, haloxyfop-sodium, HCH, hemel,hempa, HEOD, heptachlor, heptafluthrin, heptenophos, heptopargil,herbimycin, heterophos, hexachloroacetone, hexachlorobenzene,hexachlorobutadiene, hexachlorophene, hexaconazole, hexaflumuron,hexaflurate, hexalure, hexamide, hexazinone, hexylthiofos, hexythiazox,HHDN, holosulf, huancaiwo, huangcaoling, huanjunzuo, hydramethylnon,hydrargaphen, hydrated lime, hydrogen cyanide, hydroprene, hymexazol,hyquincarb, IAA, IBA, icaridin, imazalil, imazalil nitrate, imazalilsulfate, imazamethabenz, imazamethabenz-methyl, imazamox,imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr,imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium,imazaquin-methyl, imazaquin-sodium, imazethapyr, imazethapyr-ammonium,imazosulfuron, imibenconazole, imicyafos, imidacloprid, imidaclothiz,iminoctadine, iminoctadine triacetate, iminoctadine trialbesilate,imiprothrin, inabenfide, indanofan, indaziflam, indoxacarb, inezin,iodobonil, iodocarb, iodomethane, iodosulfuron, iodosulfuron-methyl,iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium,ioxynil, ioxynil octanoate, ioxynil-lithium, ioxynil-sodium, ipazine,ipconazole, ipfencarbazone, iprobenfos, iprodione, iprovalicarb,iprymidam, ipsdienol, ipsenol, IPSP, isamidofos, isazofos, isobenzan,isocarbamid, isocarbophos, isocil, isodrin, isofenphos,isofenphos-methyl, isofetamid, isolan, isomethiozin, isonoruron,isopolinate, isoprocarb, isopropalin, isoprothiolane, isoproturon,isopyrazam, isopyrimol, isothioate, isotianil, isouron, isovaledione,isoxaben, isoxachlortole, isoxadifen, isoxadifen-ethyl, isoxaflutole,isoxapyrifop, isoxathion, ivermectin, izopamfos, japonilure, japothrins,jasmolin I, jasmolin II, jasmonic acid, jiahuangchongzong,jiajizengxiaolin, jiaxiangjunzhi, jiecaowan, jiecaoxi, jodfenphos,juvenile hormone I, juvenile hormone II, juvenile hormone III,kadethrin, karbutilate, karetazan, karetazan-potassium, kasugamycin,kasugamycin hydrochloride, kejunlin, kelevan, ketospiradox,ketospiradox-potassium, kinetin, kinoprene, kresoxim-methyl, kuicaoxi,lactofen, lambda-cyhalothrin, latilure, lead arsenate, lenacil,lepimectin, leptophos, lindane, lineatin, linuron, lirimfos, litlure,looplure, lufenuron, lvdingjunzhi, Ivxiancaolin, lythidathion, MAA,malathion, maleic hydrazide, malonoben, maltodextrin, MAMA, mancopper,mancozeb, mandipropamid, mandestrobin, maneb, matrine, mazidox, MCPA,MCPA-2-ethylhexyl, MCPA-butotyl, MCPA-butyl, MCPA-dimethylammonium,MCPA-diolamine, MCPA-ethyl, MCPA-isobutyl, MCPA-isoctyl, MCPA-isopropyl,MCPA-methyl, MCPA-olamine, MCPA-potassium, MCPA-sodium, MCPA-thioethyl,MCPA-trolamine, MCPB, MCPB-ethyl, MCPB-methyl, MCPB-sodium, mebenil,mecarbam, mecarbinzid, mecarphon, mecoprop, mecoprop-2-ethylhexyl,mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl,mecoprop-isoctyl, mecoprop-methyl, mecoprop-P, mecoprop-P-2-ethylhexyl,mecoprop-P-dimethylammonium, mecoprop-P-isobutyl, mecoprop-potassium,mecoprop-P-potassium, mecoprop-sodium, mecoprop-trolamine, medimeform,medinoterb, medinoterb acetate, medlure, mefenacet, mefenpyr,mefenpyr-diethyl, mefluidide, mefluidide-diolamine,mefluidide-potassium, megatomoic acid, menazon, mepanipyrim,meperfluthrin, mephenate, mephosfolan, mepiquat, mepiquat chloride,mepiquat pentaborate, mepronil, meptyldinocap, mercuric chloride,mercuric oxide, mercurous chloride, merphos, mesoprazine, mesosulfuron,mesosulfuron-methyl, mesotrione, mesulfen, mesulfenfos, metaflumizone,metalaxyl, metalaxyl-M, metaldehyde, metam, metam-ammonium, metamifop,metamitron, metam-potassium, metam-sodium, metazachlor, metazosulfuron,metazoxolon, metconazole, metepa, metflurazon, methabenzthiazuron,methacrifos, methalpropalin, methamidophos, methasulfocarb, methazole,methfuroxam, methidathion, methiobencarb, methiocarb,methiopyrisulfuron, methiotepa, methiozolin, methiuron, methocrotophos,methometon, methomyl, methoprene, methoprotryne, methoquin-butyl,methothrin, methoxychlor, methoxyfenozide, methoxyphenone, methylapholate, methyl bromide, methyl eugenol, methyl iodide, methylisothiocyanate, methylacetophos, methylchloroform, methyldymron,methylene chloride, methylmercury benzoate, methylmercury dicyandiamide,methylmercury pentachlorophenoxide, methylneodecanamide, metiram,metobenzuron, metobromuron, metofluthrin, metolachlor, metolcarb,metominostrobin, metosulam, metoxadiazone, metoxuron, metrafenone,metribuzin, metsulfovax, metsulfuron, metsulfuron-methyl, mevinphos,mexacarbate, mieshuan, milbemectin, milbemycin oxime, milneb, mipafox,mirex, MNAF, moguchun, molinate, molosultap, momfluorothrin, monalide,monisouron, monochloroacetic acid, monocrotophos, monolinuron,monosulfuron, monosulfuron-ester, monuron, monuron TCA, morfamquat,morfamquat dichloride, moroxydine, moroxydine hydrochloride,morphothion, morzid, moxidectin, MSMA, muscalure, myclobutanil,myclozolin, N-(ethylmercury)-p-toluenesulphonanilide, nabam, naftalofos,naled, naphthalene, naphthaleneacetamide, naphthalic anhydride,naphthoxyacetic acids, naproanilide, napropamide, napropamide-M,naptalam, naptalam-sodium, natamycin, neburon, niclosamide,niclosamide-olamine, nicosulfuron, nicotine, nifluridide, nipyraclofen,nitenpyram, nithiazine, nitralin, nitrapyrin, nitrilacarb, nitrofen,nitrofluorfen, nitrostyrene, nitrothal-isopropyl, norbormide,norflurazon, nornicotine, noruron, novaluron, noviflumuron, nuarimol,OCH, octachlorodipropyl ether, octhilinone, ofurace, omethoate,orbencarb, orfralure, ortho-dichlorobenzene, orthosulfamuron,oryctalure, orysastrobin, oryzalin, osthol, ostramone, oxabetrinil,oxadiargyl, oxadiazon, oxadixyl, oxamate, oxamyl, oxapyrazon,oxapyrazon-dimolamine, oxapyrazon-sodium, oxasulfuron, oxathiapiprolin,oxaziclomefone, oxine-copper, oxolinic acid, oxpoconazole, oxpoconazolefumarate, oxycarboxin, oxydemeton-methyl, oxydeprofos, oxydisulfoton,oxyfluorfen, oxymatrine, oxytetracycline, oxytetracycline hydrochloride,paclobutrazol, paichongding, para-dichlorobenzene, parafluron, paraquat,paraquat dichloride, paraquat dimetilsulfate, parathion,parathion-methyl, parinol, pebulate, pefurazoate, pelargonic acid,penconazole, pencycuron, pendimethalin, penflufen, penfluron,penoxsulam, pentachlorophenol, pentachlorophenyl laurate, pentanochlor,penthiopyrad, pentmethrin, pentoxazone, perfluidone, permethrin,pethoxamid, phenamacril, phenazine oxide, phenisopham, phenkapton,phenmedipham, phenmedipham-ethyl, phenobenzuron, phenothrin,phenproxide, phenthoate, phenylmercuriurea, phenylmercury acetate,phenylmercury chloride, phenylmercury derivative of pyrocatechol,phenylmercury nitrate, phenylmercury salicylate, phorate, phosacetim,phosalone, phosdiphen, phosfolan, phosfolan-methyl, phosglycin, phosmet,phosnichlor, phosphamidon, phosphine, phosphocarb, phosphorus, phostin,phoxim, phoxim-methyl, phthalide, picarbutrazox, picloram,picloram-2-ethylhexyl, picloram-isoctyl, picloram-methyl,picloram-olamine, picloram-potassium, picloram-triethylammonium,picloram-tris(2-hydroxypropyl)ammonium, picolinafen, picoxystrobin,pindone, pindone-sodium, pinoxaden, piperalin, piperonyl butoxide,piperonyl cyclonene, piperophos, piproctanyl, piproctanyl bromide,piprotal, pirimetaphos, pirimicarb, pirimioxyphos, pirimiphos-ethyl,pirimiphos-methyl, plifenate, polycarbamate, polyoxins, polyoxorim,polyoxorim-zinc, polythialan, potassium arsenite, potassium azide,potassium cyanate, potassium gibberellate, potassium naphthenate,potassium polysulfide, potassium thiocyanate, potassiumα-naphthaleneacetate, pp′-DDT, prallethrin, precocene I, precocene II,precocene III, pretilachlor, primidophos, primisulfuron,primisulfuron-methyl, probenazole, prochloraz, prochloraz-manganese,proclonol, procyazine, procymidone, prodiamine, profenofos, profluazol,profluralin, profluthrin, profoxydim, proglinazine, proglinazine-ethyl,prohexadione, prohexadione-calcium, prohydrojasmon, promacyl, promecarb,prometon, prometryn, promurit, propachlor, propamidine, propamidinedihydrochloride, propamocarb, propamocarb hydrochloride, propanil,propaphos, propaquizafop, propargite, proparthrin, propazine,propetamphos, propham, propiconazole, propineb, propisochlor, propoxur,propoxycarbazone, propoxycarbazone-sodium, propyl isome,propyrisulfuron, propyzamide, proquinazid, prosuler, prosulfalin,prosulfocarb, prosulfuron, prothidathion, prothiocarb, prothiocarbhydrochloride, prothioconazole, prothiofos, prothoate, protrifenbute,proxan, proxan-sodium, prynachlor, pydanon, pyflubumide, pymetrozine,pyracarbolid, pyraclofos, pyraclonil, pyraclostrobin, pyraflufen,pyraflufen-ethyl, pyrafluprole, pyramat, pyrametostrobin,pyraoxystrobin, pyrasulfotole, pyrazolynate, pyrazophos, pyrazosulfuron,pyrazosulfuron-ethyl, pyrazothion, pyrazoxyfen, pyresmethrin, pyrethrinI, pyrethrin II, pyrethrins, pyribambenz-isopropyl, pyribambenz-propyl,pyribencarb, pyribenzoxim, pyributicarb, pyriclor, pyridaben, pyridafol,pyridalyl, pyridaphenthion, pyridate, pyridinitril, pyrifenox,pyrifluquinazon, pyriftalid, pyrimethanil, pyrimidifen, pyriminobac,pyriminobac-methyl, pyriminostrobin, pyrimisulfan, pyrimitate,pyrinuron, pyriofenone, pyriprole, pyripropanol, pyriproxyfen,pyrisoxazole, pyrithiobac, pyrithiobac-sodium, pyrolan, pyroquilon,pyroxasulfone, pyroxsulam, pyroxychlor, pyroxyfur, quassia, quinacetol,quinacetol sulfate, quinalphos, quinalphos-methyl, quinazamid,quinclorac, quinconazole, quinmerac, quinoclamine, quinonamid,quinothion, quinoxyfen, quintiofos, quintozene, quizalofop,quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl,quizalofop-P-tefuryl, quwenzhi, quyingding, rabenzazole, rafoxanide,rebemide, rescalure, resmethrin, rhodethanil, rhodojaponin-III,ribavirin, rimsulfuron, rotenone, ryania, saflufenacil, saijunmao,saisentong, salicylanilide, sanguinarine, santonin, schradan,scilliroside, sebuthylazine, secbumeton, sedaxane, selamectin,semiamitraz, semiamitraz chloride, sesamex, sesamolin, sethoxydim,shuangjiaancaolin, siduron, siglure, silafluofen, silatrane, silica gel,silthiofam, simazine, simeconazole, simeton, simetryn, sintofen, SMA,S-metolachlor, sodium arsenite, sodium azide, sodium chlorate, sodiumfluoride, sodium fluoroacetate, sodium hexafluorosilicate, sodiumnaphthenate, sodium orthophenylphenoxide, sodium pentachlorophenoxide,sodium polysulfide, sodium thiocyanate, sodium α-naphthaleneacetate,sophamide, spinetoram, spinosad, spirodiclofen, spiromesifen,spirotetramat, spiroxamine, streptomycin, streptomycin sesquisulfate,strychnine, sulcatol, sulcofuron, sulcofuron-sodium, sulcotrione,sulfallate, sulfentrazone, sulfiram, sulfluramid, sulfometuron,sulfometuron-methyl, sulfosulfuron, sulfotep, sulfoxaflor, sulfoxide,sulfoxime, sulfur, sulfuric acid, sulfuryl fluoride, sulglycapin,sulprofos, sultropen, swep, tau-fluvalinate, tavron, tazimcarb, TCA,TCA-ammonium, TCA-calcium, TCA-ethadyl, TCA-magnesium, TCA-sodium, TDE,tebuconazole, tebufenozide, tebufenpyrad, tebufloquin, tebupirimfos,tebutam, tebuthiuron, tecloftalam, tecnazene, tecoram, teflubenzuron,tefluthrin, tefuryltrione, tembotrione, temephos, tepa, TEPP,tepraloxydim, terallethrin, terbacil, terbucarb, terbuchlor, terbufos,terbumeton, terbuthylazine, terbutryn, tetcyclacis, tetrachloroethane,tetrachlorvinphos, tetraconazole, tetradifon, tetrafluron, tetramethrin,tetramethylfluthrin, tetramine, tetranactin, tetraniliprole, tetrasul,thallium sulfate, thenylchlor, theta-cypermethrin, thiabendazole,thiacloprid, thiadifluor, thiamethoxam, thiapronil, thiazafluron,thiazopyr, thicrofos, thicyofen, thidiazimin, thidiazuron,thiencarbazone, thiencarbazone-methyl, thifensulfuron,thifensulfuron-methyl, thifluzamide, thiobencarb, thiocarboxime,thiochlorfenphim, thiocyclam, thiocyclam hydrochloride, thiocyclamoxalate, thiodiazole-copper, thiodicarb, thiofanox, thiofluoximate,thiohempa, thiomersal, thiometon, thionazin, thiophanate,thiophanate-methyl, thioquinox, thiosemicarbazide, thiosultap,thiosultap-diammonium, thiosultap-disodium, thiosultap-monosodium,thiotepa, thiram, thuringiensin, tiadinil, tiafenacil, tiaojiean,tiocarbazil, tioclorim, tioxazafen, tioxymid, tirpate, tolclofos-methyl,tolfenpyrad, tolprocarb, tolpyralate, tolylfluanid, tolylmercuryacetate, topramezone, tralkoxydim, tralocythrin, tralomethrin,tralopyril, transfluthrin, transpermethrin, tretamine, triacontanol,triadimefon, triadimenol, triafamone, tri-allate, triamiphos,triapenthenol, triarathene, triarimol, triasulfuron, triazamate,triazbutil, triaziflam, triazophos, triazoxide, tribenuron,tribenuron-methyl, tribufos, tributyltin oxide, tricamba, trichlamide,trichlorfon, trichlormetaphos-3, trichloronat, triclopyr,triclopyr-butotyl, triclopyr-ethyl, triclopyricarb,triclopyr-triethylammonium, tricyclazole, tridemorph, tridiphane,trietazine, trifenmorph, trifenofos, trifloxystrobin, trifloxysulfuron,trifloxysulfuron-sodium, trifludimoxazin, triflumezopyrim, triflumizole,triflumuron, trifluralin, triflusulfuron, triflusulfuron-methyl, trifop,trifop-methyl, trifopsime, triforine, trihydroxytriazine, trimedlure,trimethacarb, trimeturon, trinexapac, trinexapac-ethyl, triprene,tripropindan, triptolide, tritac, triticonazole, tritosulfuron,trunc-call, uniconazole, uniconazole-P, urbacide, uredepa, valerate,validamycin, valifenalate, valone, vamidothion, vangard, vaniliprole,vernolate, vinclozolin, warfarin, warfarin-potassium, warfarin-sodium,xiaochongliulin, xinjunan, xiwojunan, XMC, xylachlor, xylenols,xylylcarb, yishijing, zarilamid, zeatin, zengxiaoan, zeta-cypermethrin,zinc naphthenate, zinc phosphide, zinc thiazole, zineb, ziram,zolaprofos, zoxamide, zuomihuanglong, α-chlorohydrin, α-ecdysone,α-multistriatin, and α-naphthaleneacetic acid.
 17. A pesticidalcomposition according to claim 12 further comprising one or morebiopesticides.
 18. A pesticidal composition according to claim 12further comprising a seed.
 19. A process for controlling pest comprisingapplying a pesticidal composition according to claim 12 to a locus tocontrol a pest, in a sufficient amount to control said pest.
 20. Aprocess according to claim 19 wherein said pest is selected from ants,aphids, beetles, bristletails, cockroaches, crickets, earwigs, fleas,flies, grasshoppers, leafhoppers, lice, locusts, mites, moths,nematodes, scales, symphylans, termites, thrips, ticks, wasps, andwhiteflies.